Plan a romantic trip or a family vacation to Chicago to enjoy many fun attractions the city has to offer. Visit Shedd Aquarium, ride the Navy Pier Ferris wheel, and see 200 animal species at the Lincoln Park Zoo.
Head to the Millennium Park’s Bean where you can stand in front of the giant bean-like sculpture with a shiny reflective surface and take a perfect vacation photo. The hotels and inns that made our list all offer great service and many unique features, from relaxing spas and indoor pools to companion goldfish and stunning city views. Here are the best romantic Chicago vacation ideas.
»Hotel Monaco Chicago
Hotel Monaco Chicago, originally built in 1912, is located Downtown near the North Michigan Avenue shopping district and the Loop business district. Enjoy complimentary morning coffee and tea service, hosted evening wine hour and complimentary high-speed WiFi for Kimpton Karma Rewards members. Hotel Monaco Chicago is one of the best pet-friendly hotels in Chicago since the hotel has no fees or size restrictions for pets. The staff can deliver a complimentary goldfish to your guest room for company which kids will love.
There are 191 guest rooms furnished with a 37" LCD flat screen TV with cable access, Frette linens and luxurious bath amenities. For tall guests, there are "Tall Rooms" with extra-long beds and raised showerheads. South Water Kitchen serves delicious Midwestern cuisine, available 24 hours a day. The Hosted Wine Hour in the lobby of the hotel from 5 to 6 p.m. is a favorite with visitors and locals alike. Room rates start from US $199 per night.
225 N Wabash Ave, Chicago, Illinois, Phone: 312-960-8500 (website)
More vacation ideas: Best Romantic Things to See & Do in Chicago.
Getaways: From NYC, Ohio, TX, PA, CA, San Francisco, Seattle, Atlanta, Chicago
»Intercontinental Chicago Magnificent Mile
Intercontinental Chicago Magnificent Mile provides a great base for exploring the city because of its central location, stylish rooms and spectacular views. Families can enjoy extra space by booking one of the spacious suites which feature French doors that separate the living room from the bedroom.
Two 37-inch flat screen TVs in the suite ensure that everyone will get to watch what they like: cartoons for kids and a TV show for parents. There is also a bar area and an I-Home Docking station. There are several dining options at the hotel: Michael Jordan's Steak House, contemporary dining at the Continental, wine & cheese at Eno and a Starbucks shop. Rooms start at $179.
505 N Michigan Ave, Chicago, Illinois, Phone: 312-944-4100 (website)
Next read: Best Time to Visit Chicago, Illinois & Other Travel Tips
Points of interest in: Sanibel Island, Newport Beach, Orlando, Boston, Houston
Acme Hotel is a hip getaway with modern rooms and a central location in downtown Chicago. High-tech amenities include 46-inch internet-ready smart TV's which let you plug in your own Apple and PC devices, super-fast & free 100 MB internet, a free Google Glass program, and top-of-the-line wireless audio systems. Guest rooms are equipped with a mini-bar and snack tray, while suites offer a wet-bar and a microwave.
Acme Hotel suites offer plenty of space for a girlfriends' getaway or a family vacation. Other unique amenities you will find at this hotel include free morning coffee delivery, "Knock and Drop" room service which lets you order from the bakery located in the lobby, and an old world cocktail lounge for chatting with fellow travelers. Rooms are very affordable, starting at $95 per night.
15 E Ohio St, Chicago, Illinois, Phone: 312-894-0800 (website)
Fun destinations: Bar Harbor, Galena, Irving, Irving, Erie, Quebec City
Fun places to visit & what to do last minute: Great Attractions & Free Activities
»Fairmont Chicago Millennium Park
The Fairmont Chicago rises high above Grant Park and is located near the Magnificent Mile shopping area, many of the city's cultural attractions, and the business district. The hotel recently completed a five year $60 million transformation and features a new lobby and luxurious spa. There are 692 guest rooms and suites furnished to give its guests a residential feel. Many of the hotel rooms have seating areas and some offer spectacular views of the city and the Chicago River.
The 11,000-square-foot spa has eight treatment rooms and offers a full range of spa services, including massages for men and women, facials, skincare and body treatments. Hotel rooms are decorated with earthy shades, colorful throw pillows and original artwork by Warwick Orme. All guest accommodations have luxurious marble-tiled bathrooms with separate tubs and showers with rainfall-style showerheads. A 42" high definition TV, iPod docking station, Nespresso Coffee Makers, high speed wireless Internet access and stunning views of the Chicago lakefront are also standard.
Things to see in: Helena, El Paso, Milford, Jim Thorpe, Kennett Square, Rochester
The 420 sq ft Fairmont Room has either One King or Two Double Beds. If you want views of Grant Park, Millennium Park and Lake Michigan, ask for one of the Deluxe Guestrooms. Luxurious 700-square-foot Fairmont Suites feature unique decor such as hanging lamp and Warwick Orme art. These accommodations can easily be turned into a two-bedroom by booking an adjoining room, perfect for groups and families. Each of the 5 Grand Suites offers between 900 and 1,850 square feet of space with a spacious living room area great for entertaining. Ask for a whirlpool tub if you are planning a romantic getaway. Some of the unique touches include a Kauai grand piano, kitchen or wet bar and fireplace. Doubles start at $235 USD (312-565-8000, website).
"23 Best Romantic Chicago Vacation Ideas" Back to Top
Vacation ideas: Pigeon Forge, Columbus, Southwest vacations, From Dallas, Jacksonville, Last Minute, Spa
»Hotel Allegro Chicago
Hotel Allegro Chicago is a boutique hotel located in the heart of the financial and theater district. The downtown Loop Theatre District offers many activities and attractions, including shopping along the Magnificent Mile, the Art Institute, Navy Pier, and the Lincoln Park Zoo. The hotel has 483 guestrooms with a 37" LCD HD flat-screen TV, Bigelow bath amenities and iHome docking station. Guests receive complimentary morning coffee and tea in the lobby, as well complimentary in-room yoga accessories for the duration of their stay.
If you forget any of the travel essentials, no worries. The front desk can supply you with nearly anything, from a sewing kit to a mobile charger. 312 Chicago serves authentic Italian cuisine created by Executive Chef Luca Corazzina. The hotel is easily accessible by car and offers guests valet and self-park service. Room rates start from $119 per night (866-672-6143, 312-236-0123, website).
Vacation Ideas: Getaways from New Orleans, Philadelphia Tours, Annapolis Restaurants, Sarasota Restaurants
Vacations for Couples, Packages & Date Night Ideas: Best Romantic Getaways
»Lang House Bed and Breakfast on Sheridan
Lang House is a romantic bed and breakfast built in 1919. With five individually decorated suites to provide a relaxing traditional bed and breakfast experience, the rooms feature pillow topped beds and luxurious linens to provide the comfort you desire. Start your day with a continental breakfast that includes delightful pastries from local shops while sitting in one of the shared areas or enjoying the patio.
The onsite Spa and Sauna offer a great way for you and your partner to unwind and relax. The most delightful part of your stay will be the pampering provided by innkeepers Bruce and Wayde. Rates start at $159 per night.
7421 N Sheridan Rd, Chicago, Illinois, Phone: 773-764-9851 (website)
More trip ideas: Arkansas, Bismarck, Kirkland, Pierre, Salem, Bozeman
Get away with kids: Best Family Vacations, Best Beaches, NC, MI, UT, MD, GA, Hawaii
»Trump International Hotel & Tower, Chicago
Trump International, Chicago has 339 rooms with spectacular city views through their floor-to-ceiling windows. The tower soars 92 stories above the city. Guest accommodations feature fully equipped kitchens, great for families. The Spa measures 23,000 square feet in size and has treatment rooms overlooking the city skyline. Signature therapies utilize gem-infused oils and Kate Somerville skin care. There are 53 Spa guestrooms on two dedicated floors with direct access to the Spa.
These rooms feature calming decor and relaxing amenities such as heated eye and neck pillows. Grand Deluxe Suites are the most spacious, ranging from 1,663 to 3,150 square feet in size. They overlook Lake Michigan, the river and the city skyline. Amenities include 42-inch flat-panel HDTVs, Bose, separate living room, a dining are, and a fully equipped kitchen. Guests have access to the luxury Attache services. The restaurants serve imaginative cuisine and sophisticated cocktails. Room rates start at $460 per night (312-588-8000, website).
Things to See in: Cape Canaveral, Juneau, Lowell, Lakeland, Vancouver, Santa Clarita
"23 Best Romantic Chicago Vacation Ideas this Weekend" Back to Top
San Antonio, TX: Things to Do in San Antonio, Restaurants, San Antonio Zoo, When to Go, San Antonio Museum of Art, San Antonio Missions, San Antonio Botanical Garden, McNay Art Museum
»Hard Rock Hotel Chicago
If you are set on rubbing elbows with celebrity guests, check into Hard Rock Hotel Chicago. Located downtown, the hotel is frequented by musicians and celebrities who like the uniquely decorated luxury suites. The hotel offers great city views from its rooms, suites, restaurants and bars located in the 40-story hotel tower. There is an outdoor swimming pool with luxury cabanas. Pets are welcome and receive special amenities during the stay, including a specially designed dog tag, bowl, dog toy, and natural treats and meals.
The hotel concierge can help you plan a tour of the city so that you can bring your dog with you. Concierge services include help with booking massages, limo service, restaurant reservations and tickets to some of the most popular shows in town. Dining options include Angels & Kings Chicago which serves classical American cuisine and Chuck's: A Kerry Simon Kitchen which offers a more contemporary menu. The hotel is popular for bachelor and bachelorette parties with staff standing by to help you plan your dream evening. Rooms start at $99 per night (312-345-1000, website).
Vacation Ideas: Montclair, Roswell, Lake Charles, Trips Near Miami, Weekend in CT
Best attractions & points of interest in: Destin, Sacramento, Louisville, Raleigh, Norfolk
"23 Best Romantic Chicago Vacation Ideas & Free Things to Do on a Rainy Day" Back to Top
Hotel Burnham is located in a National Historic Landmark building at the corner of State and Washington Streets.
Guests have easy access to the city's financial and theatre districts as well as shopping and dining along the Magnificent Mile. If you are looking for a pet-friendly trip idea, the hotel welcomes well behaved pets.
There are 122 guest rooms and suites at the hotel, luxuriously decorated in rich fabrics of gold and blue. The rooms feature magnificent views of the city skyline. Ask for one of the corner rooms which have great views from both windows.
Atwood serves delicious American comfort food for breakfast, brunch, lunch and dinner. Room rates start from US $110 per night (877-294-9712, 312-782-1111, website).
Weekend on the beach: Flagler Beach, Huntington Beach, Rehoboth Beach, Nassau, San Clemente
Holiday ideas: Birthday, Anniversary Ideas, Secluded, Girlfriend Getaways, Valentine's Day, Easter
»The Peninsula Chicago
Stay at The Peninsula Chicago to enjoy its spa with spectacular views of Lake Michigan and central location in the heart of Chicago's Magnificent Mile. The 339 luxury guest rooms and suites, located in a 20-story tower, feature marble bathrooms with a separate shower and soaking tub. The rooms measure at least 530 square feet in size so you will have plenty of space on your trip. Many rooms have excellent city views. The Peninsula Spa is a 14,000-square-foot spa and fitness area located on the 19th and 20th floors. Swim a few laps in the glass enclosed swimming pool overlooking Michigan Avenue, soak in one of the whirlpools and visit the rooftop sundeck after enjoying a healthy meal. The spa offers personal training, nutrition counseling and an array of therapeutic treatments, including Swedish massage, Shiatsu, Nan Shin Pregnancy Massage, reflexology, couples massage, facials and body treatments. You can also choose from a number of customized packages.
Fine dining is offered at the Asian-style Shanghai Terrace on the 4th floor, and Avenues Restaurant which serves sea food and features an exhibition kitchen. Avenues also has a private dining room that can accommodate up to 12 people. The Terrace, located on the fourth floor features views of the city skyline. The Terrace serves cocktails and light fare in an outdoor setting during the summer months. Doubles from $575 USD, depending on season and availability. Weekends are generally less busy, except certain holiday weekends (866-288-8889, 312-337-2888, website).
Top attractions in: Sacramento, Phoenix, Salt Lake City and Milwaukee.
Top points of interest in: Nashville, San Juan, Austin, Boulder, Indianapolis
»Waldorf Astoria Chicago
The Waldorf Astoria Chicago is a luxury getaway with 188 guest rooms and suites.
There are only 10 guest accommodations per floor, each measuring on average 890 square feet in size, giving guests more privacy. Relax next to you own private fireplace and luxuriate in white Carrera marble bathrooms with soaking tubs, separate showers, dual vanities and inset LCD televisions. Guest accommodations feature 460-thread count Italian linens on the beds, and furnished terraces.
The health club has a mosaic-tiled lap pool, treatment rooms and a state of the art fitness center. Choose from body wraps, massage, facials, Pilates and more. The ballroom can be rented for weddings. The venue has silk-covered walls, floor-to ceiling windows with custom drapery, and an intimate terrace provides a romantic setting for a glamorous wedding.
You will be close to the shops along Michigan Avenue, also known as "The Magnificent Mile," and Oak Street. Room rates start at $495 per night. website)
Island Getaways in the U.S.: Tybee Island, Dauphin Island, Catalina Island, Fire Island
Best attractions in: Cincinnati, Salt Lake City, Chapel Hill, Minneapolis, Mesa, Fort Collins, Erie, Santa Fe
»W Hotel Chicago Lakeshore
A great reason to visit W Chicago Lakeshore is the hotel's roof-top lounge Whiskey Sky with spectacular views of the city skyline and Lake Michigan. The property is located near the Navy Pier, within walking distance of Ontario Beach and Michigan Avenue shopping. There are 556 stylish guest rooms and suites, equipped with high speed internet access, an oversized desk, Fax/Copier/Printer, and the signature W hotels bed. Each room includes Aveda bath amenities and a "Munchie Box." Guests can choose from lakeview and city view rooms and suites.
In addition to Whiskey Sky, the hotel has a Zen-like Living Room, and a signature restaurant. Wave Restaurant, open all day, serves Mediterranean cuisine in a casual setting. Room rates, which vary by season, start from $199 per night (312-943-9200, website).
More vacation ideas: Best Things to Do in Chicago with Kids.
More places to visit: Jasper, Reykjavik, South Bend, North Dakota, Nebraska, Niagara Falls, New York City, Kingston, Hudson
»Welcome Inn Manor
If you are looking for a traditional bed and breakfast experience and are interested in staying in a Queen Anne styled home built in 1893, you will not want to miss a chance to visit the Welcome Inn Manor. With seven suites furnished with timely antiques and historic art pieces, the establishment will fill you with a sense of the history from the moment you walk in. During your stay, you will be pampered with amenities such as Wi-Fi access, flat screen TVs, fireplaces, and pillow-top mattresses.
Individually decorated common areas, including a formal dining area, sitting rooms, a family parlor and a community kitchen, create a feeling of peaceful relaxation. Each day, a fresh, handmade breakfast is created especially for guests, and it will surely be one of the highlights of your stay. Rates start at $179.
4563 S Michigan Ave, Chicago, Illinois, Phone: 312-493-2953 (website)
Fun things to do in: Omaha, Jackson, Providence and Reykjavik, Iceland.
"23 Best Romantic Chicago Vacation Ideas with Kids" Back to Top
Scottsdale, AZ: Things to Do in Scottsdale, Fairmont Scottsdale Princess, Best Time to Visit Scottsdale, Hyatt Regency Scottsdale, The Phoenician, Sanctuary Camelback Mountain, Camelback Inn, The Boulders, Winter Vacations, More Scottsdale resorts
»House 5863 Bed and Breakfast
House 5863 B&B in the Edgewater Andersonville neighborhood has five bright, spacious rooms with modern amenities and gorgeous design. The continental breakfast is a tasty delight. All common areas are comfortable, allowing you to completely enjoy your stay.
Staff members are available to answer questions and provide help but they also give you the space you need. During your stay, you will not want to miss relaxing in the beautifully maintained gardens, which are a great place for a wedding or party. Rates start at $99.
5863 North Glenwood, Chicago, Illinois, Phone: 773-682-5217 (website)
Next read: Chicago to Indianapolis
Things to do with kids in: Portland, Maui, San Francisco, DC, Taos, Houston, Family Getaways
»Ruby Room Inn and Salon
Located in the Wicker Park District of Chicago, the Ruby Room Inn and Salon is an ideal escape for relaxing, unwinding, and disconnecting on your weekend trip. This eight-room bed and breakfast features antiques, marble showers, and luxurious linens so that guests feel comfort and tranquility during their stay.
You will find that a hidden perk of staying at the Ruby Room Inn is the absence of TV’s and phones in the rooms, allowing you to fully appreciate the atmosphere. After a day of exploring the city, pamper yourself with a trip to the salon and enjoy a Deluxe Arcona facial, which will leave you with a calm sense of bliss. You will have access to a kitchen and the staff is always ready to provide restaurant suggestions.
1743-45 W. Division Street, Chicago, Illinois, Phone: 773-235-2323 (website)
More vacation ideas: Romantic Getaways in NJ and Wisconsin
Romantic things to do: Paris, Maui, East Coast, NY, IL, Tempe, Calgary, Encinitas, Charleston SC, Healdsburg
»The Old Chicago Inn Bed and Breakfast
If you are looking for a classic Chicago experience that includes an 1920’s speakeasy lounge, the Old Chicago Inn Bed and Breakfast is a great choice. The establishment is conveniently located four blocks from Wrigley Field, so that you can enjoy an afternoon walk to a game or jump onto the El line and head to the Chicago Loop. Each room is quaintly decorated with antiques, and a main highlight at the inn is an impressive Chicago-themed library where you can spend hours lost in another era.
The Old Chicago Inn features ten uniquely decorated rooms that include free Wi-Fi, and guests are provided with gym passes. Most of the rooms feature private bathrooms. During your stay, you will want to start each morning enjoying a continental breakfast and end each day with a dinner at Trader Todd’s. Rates start at $80 per night.
3222 N. Sheffield Ave, Chicago, Illinois, Phone: 773-472-2278 (website)
Vacation ideas in: Montreal, Richmond, Sedona, Buffalo, Galveston, Knoxville
»Ray's Bucktown Bed and Breakfast
Providing a traditional European bed and breakfast experience, Ray’s Bucktown B&B is a unique place to stay while visiting Chicago. The establishment is just steps away from fine dining and shopping, and you can easily access all that Chicago has to offer. The hotel features 11 spacious, comfortable and modern rooms with Wi-Fi access, free parking, HDTV with DVR’s, luxurious private bathrooms, pillow topped beds; each moment is its own a cozy, happy escape.
Mornings begin with a cooked to order breakfast prepared for each guest, ensuring that everyone starts the days off right. Ray’s Bucktown B&B also has a community office space, a steam, room and sauna to meet all your travel needs. Rates start at $129.
2144 N Leavitt St, Chicago, Illinois, Phone: 773-384-3245 (website)
"Visit: 23 Best Romantic Chicago Vacation Ideas" Back to Top
More Trips: Romantic Getaways in Ohio, Florida Destinations, California Destinations, Places to Visit in Arizona, Portland, Corpus Christi
Built as an 1890’s coach house, Bucktown House boasts modern, spacious amenities and fully furnished apartments, and it provides a level of comfort that will exceed your expectations for your Windy City getaway. Ideal for a stay lasting a few days or for long-term visits, Bucktown House allows you to retreat to your apartment and feel truly at home daily. Each of the four houses was refurbished to provide everything you need to feel at home.
The rooms feature modern bathrooms and fully equipped kitchens, and after an exciting day of shopping or visiting museums, you can enjoy a warm and cozy evening in with friends and family. Apartment features include Internet access, flat screen TVs, DirectTV, and iPod docks.
2216 W Palmer St, Chicago, Illinois, Phone: 312-313-0505 (website)
More Trips: Romantic Weekend Getaways, North Carolina Destinations, Weekend Getaways from SF, Weekend Getaways from NYC, Texas, St. Petersburg, Catalina Island, MA
»The Villa Toscana Bed and Breakfast
Booking a trip to The Villa Toscana is an opportunity to stay in a traditional Victorian-home built in 1892. This artistically decorated bed and breakfast located in the heart of Boys Town and The East Lakeview Neighborhood is a perfect getaway that allows guests to enjoy the feel, sites, and flavors of Chicago. Each of the eight comfortable rooms features unique art themes, from Moroccan art themes to art deco.
Rooms also have centrally controlled air conditioning, Internet access and a digital TV. Several of the rooms have shared bathrooms. Start your day with a continental breakfast in the kitchen or in the beautiful garden. During peak seasons, there is a 3-night minimum stay on weekends. Rates start at $129 per night.
3447 N. Halsted Street, Chicago, Illinois, Phone: 773-404-2416 (website)
More places to stay in Chicago: Virgin Hotels Chicago and the Palmer House Hilton.
Family Weekend Trips: North Carolina, From NYC, Minnesota, Wisconsin, East Coast, West Palm Beach, North Carolina, West Coast, East Coast
»Wicker Park Inn
If you are looking for a modern, upscale bed and breakfast with spacious studio suites and apartments featuring wood floors and exposed brick walls, take a look at the Wicker Park Inn. Located 3.2 miles from the Inner Loop in Chicago, this property is an ideal retreat if you are in the area for work, exploring the area, or travelling with your partner. A tasty and impressive continental breakfast is available in the kitchen where you will also find delightful treats and snacks throughout the day.
You will be pampered throughout your stay with access to a local gym, wireless Internet access, private bathrooms, and free parking. The Wicker Park Inn requires a 3-night minimum stay on most weekends. Rates start at $179.
1329 N Wicker Park Ave, Chicago, Illinois, Phone: 773-486-2743 (website)
More trips: Great Weekend Getaways, Anniversary Ideas, Romantic Getaways in NJ, California Vacation, For Couples, Things to Do in Tampa
23 Best Romantic Chicago Vacation Ideas
- Hotel Monaco Chicago, Photo Credit: Kimpton Hotels
- Intercontinental Chicago Magnificent Mile
- Acme Hotel, Photo Credit: Acme Hotel
- Fairmont Chicago Millennium Park
- Hotel Allegro Chicago, Photo Credit: Kimpton Hotels
- Lang House Bed and Breakfast on Sheridan, Photo Credit: Lang House
- Trump International Hotel & Tower, Chicago
- Hard Rock Hotel Chicago, Photo Credit: Hard Rock Hotel Chicago
- Hotel Burnham, Photo Credit: Kimpton Hotels
- The Peninsula Chicago
- Waldorf Astoria Chicago, Photo Credit: Waldorf Astoria Chicago
- W Hotel Chicago Lakeshore, Photo Credit: W Hotel Chicago Lakeshore
- Welcome Inn Manor, Photo Credit: Welcome Inn Manor
- House 5863 Bed and Breakfast, Photo Credit: House 5863 Bed and Breakfast
- Ruby Room Inn and Salon, Photo Credit: Ruby Room Inn and Salon
- The Old Chicago Inn Bed and Breakfast, Photo Credit: The Old Chicago Inn Bed and Breakfast
- Ray's Bucktown Bed and Breakfast, Photo Credit: Ray's Bucktown Bed and Breakfast
- Bucktown House, Photo Credit: Bucktown House
- The Villa Toscana Bed and Breakfast, Photo Credit: The Villa Toscana Bed and Breakfast
- Wicker Park Inn, Photo Credit: Wicker Park Inn
- Cover Photo Credit: Courtesy of FotoMak - Fotolia.com
Chicago Vacation Tips
Chicago, Illinois is a fun destination to visit, giving visitors a choice of attractions, restaurants, shopping, unique hotels, cafes, art and great views. The city has two rivers and is located along beautiful Lake Michigan. The Chicago River flows through downtown - take a river cruise for a unique perspective of the Windy City. If you are on a budget, there are many free attractions in the city, including the zoo for kids, several museums and outdoor attractions. Our travel includes vacation tips, highlights, deals, packages and other ideas.
Practical Travel Tips for the Trip
Many hotels offer deals and specials on weekends when there are fewer business travelers, so it’s a great idea to plan a weekend getaway to the city. Couples can look for romantic packages that include pampering at a spa, dinner and VIP treatment. Families can ask about room specials when booking two rooms, discounts or free meals for kids and free parking.
Don’t underestimate packages that include free breakfast, free internet access and free parking because those fees can really add up, especially if you are staying a few nights. Can you find all inclusive vacation packages in Chicago? Check major airline sites, including Delta, US Airways and Spirit Airlines for offers that include airfare, rooms and event tickets.
- What is the Best Time to Go? The best time to visit is in the fall – springs are rainy, summers hot and humid, and winters very cold. Although Chicago is known as Windy City, the nickname does not refer to the weather but rather to the turbulent politics of the 1800s. The city is actually not particularly windy as compared to other American cities.
- How Do I Get There? You can drive, take the train or fly to Chicago O'Hare and Midway Airports. Airlines that fly here include Spirit Airlines, American, US Air and Delta. International airlines include Lufthansa, Swiss, Austrian Airlines, Finnair, SAS, Turkish Airlines, Air France and LOT. Should you fly, drive or take the train? Flying can save you time which you can spend relaxing and enjoying the city. The answer will depend on your personal preferences, cost and the travel distance.
- Getting to the City from the Airport: If you are arriving by plane, there is public transportation from the airports to the city and is the cheapest option. Blue Line train service operates from O'Hare to downtown and takes 40 minutes. Orange Line train service operates from Midway to downtown and takes 25 minutes.
- Can I Travel by Train? You can reach the city by train quite easily since it's a main hub for Amtrak. Cities that are well connected with Chicago via trains include New York, Seattle, New Orleans, San Francisco and Denver. If you are planning a trip from one of those cities, train travel is a good option.
- How Much will the Hotel Room Cost? This is not the cheapest city to visit, with room rates starting at around $145 USD per night, although you can usually get a last minute deal. Luxury hotels cost $200 and over, depending on the location. If you want to stay in the heart of the action, the cost will be higher. Look for packages that include theater tickets, free breakfast, complimentary parking and more.
- How Much will Airline Tickets Cost? Should you fly, drive or take the train? Flying can save you time which you can spend relaxing and enjoying the city. The answer will depend on your personal preferences, cost and the travel distance.
- What are the Best Events and Festivals in Chicago, IL? Some of the top city festivals to attend include Chicago International Film Festival, Grant Park Music Festival and Taste of Chicago. Many hotels will offer packages during the major events, so be sure to check their web sites for current offers which include event tickets and other perks.
There are many fun trips to take within a few hours of the city. Whether you are looking for a place to stop on your road trip or want to get to know the area around the city, check out our page on quick weekend trips and resort ideas from Chicago. You can plan a romantic getaway to Chicago and stay in one of the five star hotels on the Magnificent Mile, getting pampered from head to toe at a luxury spa. Or go on a family trip and ride the 150-foot Navy Pier Ferris wheel which has awesome river views. Honeymooners can have a romantic dinner high above in the sky at the John Hancock Center and see a fun show at the century-old Chicago Theatre. There are many great restaurants where you can celebrate a special occasion such as an anniversary or a birthday. Getting married in Chicago is easy as well, with most hotel offering in-house wedding planners who can help you plan your dream wedding.
What are some of the best attractions in Chicago?
From museums and art galleries to street cafes and parks, there is plenty to see and do. Design your itinerary based on how much time you plan to spend in the city. Here are some of the top must see attractions.
- The Magnificent Mile: Stroll down the Magnificent Mile, a stretch of Michigan Avenue where you can see some of the tallest skyscrapers in the U.S. This is the prime area of the town for first time and returning visitors, letting you experience the city in all its glory. You will recognize famous buildings, shops and hotels on your walk.
- The John Hancock Center: The John Hancock Center Is the 7th tallest building in the United States, located on Michigan Avenue. On a clear day, you can see up to four different states from the 360-degree observatory located 1,100 feet up in the air. If you are planning a romantic celebration, dine at The Signature Room on the 95th Floor which overlooks Lake Michigan.
- Chicago Theatre: See a comedy, magic show or a concert at the historic Chicago Theatre which was built in 1921 and is listed on the National Register of Historic Places. Call ahead for tickets – some shows are very popular and tickets sell out, especially during the holidays.
- Navy Pier: The family-friendly Navy Pier draws the crowds with the IMAX theater, a 150-foot Navy Pier Ferris wheel and dinner cruises which offer a unique perspective of the city. It you are looking for things to do with kids, this is a must-see attraction. Ride the Navy Pier Ferris Wheel and enjoy some of the best views of Chicago lakefront and skyline. Visit The Chicago Sports Museum (admission is free) to see artifacts and relics of famous athletes.
- Wrigley Field: See the Chicago Cubs play at Wrigley Field which has an ivy covered brick outfield wall and a hand turned scoreboard. It’s a good idea to buy your tickets before you get there, so that you have a good choice of seats.
- Chicago Field Museum: Take the kids to see natural history exhibits at the Chicago Field Museum, including the best preserved T-rex in the world. This is a popular attraction for both kids and adults – you could spend a whole day here, exploring and discovering new things.
The National Museum of Mexican Art: Located at 1852 W. 19th St., the museum houses one of the largest collections of Mexican art in the United States. You will be able to see folk art, drawings, prints, paintings, sculptures and 7,000 other unique pieces of art. Temporary exhibitions change frequently and highlight Mexico’s history and Mexican communities in the U.S.
- Taste of Chicago: During the summer, Taste of Chicago in Grant Park lets you sample food from 70 vendors, including cheesecake, hot dogs and more. If you wonder what Chicago hot dogs taste like – and who doesn’t, they’ve been featured in so many movies – this is a great place to get a taste.
- Lincoln Park Zoo: The awesome city zoo has free admission – one of the few that offers this in the world. You can see over 200 different species of animals, including a beautiful polar bear swimming in the water. Take a walk through the zoo and let your kids identify animals they’ve been learning about in school. If you have a baby in the stroller, the zoo is easy to get around. Afterwards, have a snack and rest your feet before continuing your journey through this exciting city.
- Millennium Park’s Bean: Take a photo under the Millennium Park’s Bean, a unique giant sculpture with a mirror surface. If you are looking for the perfect spot for a Christmas photo, this famous attraction is just the spot. Stand underneath it or right next to it for an interesting family photo with a reflection. Millennium Park is located just south of Michigan Avenue, so you will reach it easily after strolling along the Magnificent Mile. Have a picnic in the park, cross its amazing bridge designed by Frank Gehry. Outdoor concerts are held under the metallic band shell of the Jay Pritzker Pavilion. Crown Fountain is another unique spot in the park and projects images of Chicagoans during the summer months.
- Willis Tower: Willis Tower (formerly known as Sears Tower) was the tallest building in the world when it was completed in 1973. Currently it is the second-tallest building in the U.S. Most visitors head to this famous building’s observation deck to enjoy panoramic views of the city skyline. Is it worth the wait? If you get there early on a weekday, the line should not be too bad.
- Lakefront Esplanade: Lakefront Esplanade is a favorite with active singles and couples, offering a scenic jogging, walking, biking and skating path with a view of the Museum Campus.
- Museum Campus: You can spend a whole day at the Museum Campus, visiting the Shedd Aquarium, Field Museum, Adler Planetarium and Soldier Field.