24 Best One Day Trip Ideas in Chicago

By VI Staff on October 14, 2019

Chicago is the American Midwest's most populous and bustling metropolis, known around the world for attractions such as its lively family-friendly Navy Pier complex, upscale Magnificent Mile shopping district, and record-breaking John Hancock Tower skyscraper. While millions of visitors travel to the city each year to catch a glimpse of its most popular attractions, the city also has a plethora of activities and destinations to offer tourists looking for off-the-beaten-path day trip outings.

1.The Chicago Lakefront Trail

The Chicago Lakefront Trail is a shared-use walking and cycling path spanning along Chicago's Lake Michigan coastline, stretching for 18.5 miles past the city's Lincoln, Grant, Burnham, and Jackson Parks and a number of seasonal public beaches. The trail, which was designated in 1963 as the city's first official bicycle path, was recently renovated in 2018 in an effort to reduce congestion. Major attractions accessible via the trail include the city's Museum of Science and Industry, McCormick Place, Navy Pier, and Belmont and Monroe Harbors. Several dog parks are also accessible via the trail, along with the city's 31st Street, Grant Park, and Wilson Avenue skate parks. Trail users looking to avoid crowds can take the Navy Pier Flyover, which avoids congestion at the intersections of Grand Avenue and Illinois Street.

2.The Driehaus Museum

The Driehaus Museum is a living history museum in Chicago's Near North Side neighborhood, converting the 1883 Samuel M. Nickerson House into a recreation of the splendor of the American Gilded Age. The National Register of Historic Places-listed museum has been open to the public since 2008, showcasing the architecture and interior design of the Gilded Age with pieces sourced from the personal fine and decorative arts collection of Chicago philanthropist Richard H. Driehaus. Works on display include pieces from Belle Epoque artists such as Édouard Colonna and the Herter Brothers, along with one of the world's most noted collections of Tiffany decorative works and stained glass pieces. Visitors can enjoy guided and self-guided tours daily at the museum, including an audio tour using Acoustiguide technology. Public programming includes an annual turn-of-the-century-themed murder mystery dinner event and a quarterly jazz concert series.

40 E Erie St, Chicago, IL 60611, Phone: 312-482-8933

3.Garfield Park Conservatory

Garfield Park Conservatory is one of the largest conservatory and botanical garden parks in the United States, originally created in 1907 by landscape architect Jens Jensen. The facility, which was designed as an attempt to create the world's largest publicly-owned botanical conservatory, spans more than 4.5 acres today in Chicago's Garfield Park, presenting eight indoor garden displays showcasing a wide variety of exotic and native plant species. It has been named today as one of the American Institute of Architects' 200 Great Places in Illinois and has won significant international museum awards, including the prestigious National Medal for Museum and Library Services. Visitors can enter the conservatory for free daily and view notable plant holdings, including a collection of bicentennially-aged cycads and an expansive palm tree collection.

300 N Central Park Ave, Chicago, IL 60624, Phone: 312-746-5100

4.Chicago's Navy Pier

Chicago's Navy Pier is one of the American Midwest's most popular tourist attractions, overlooking Chicago's gorgeous Lake Michigan shoreline for a six-block stretch within the city's Streeterville neighborhood. The venue, which was originally developed as the city's Municipal Pier in 1915, was renovated into a retail and entertainment center in 1995 and attracts over nine million visitors each year today. 50 acres of retail, dining, and family attractions are offered at the pier, including the newly-added Centennial Wheel, a beautiful 200-foot observation wheel overlooking the waterfront. Other attractions include the family-friendly Pier Park amusement park, the Amazing Chicago's Funhouse Maze, the Chicago Shakespeare Theater, and the Chicago Children's Museum.

600 E Grand Ave, Chicago, IL 60611, Phone: 312-595-7437

5.The American Writer's Museum

The American Writer's Museum is a new museum in Chicago celebrating the history and legacy of America's greatest writers, opened to the public in May of 2017. The museum, which was modeled after the Dublin Writer's Museum, is the home of the Wintrust Chicago Gallery, which honors seminal figures in the city's literary community, with a focus on how the city's authors have pushed social boundaries and served as positive agents of social change in America. At the museum's Children's Literature Gallery, young visitors can enjoy interactive exhibitions, including tabletop reading screens. Other exhibitions include the Nation of Writers literary timeline and the Mind of a Writer gallery, which offers wordplay activities and other games to help young writers hone their creative and literary skills.

180 N Michigan Ave, Chicago, IL 60601, Phone: 312-374-8790

6.Dreambox Gallery and Studio

Dreambox Gallery + Studio is one of Chicago's hottest contemporary art galleries, opened in 2003 in a space located behind the Cup and Spoon coffee house in the city's West of Western district. The gallery, which was founded by Iwona Biedermann, strives to showcase the diversity and creativity of Chicago's emerging and established artists working in a variety of mediums. Rotating exhibitions throughout the year encourage a dialogue between artists and the community, with an emphasis on multiculturalism in visual art, poetry, and music. The gallery is open on Friday and Saturday from 12-4pm, or by appointment. During the summer months, the gallery also operates a public urban garden space.

2415 W North Ave, Chicago, IL 60647, Phone: 773-292-0419

7.Chicago for Chicagoans

Chicago for Chicagoans offers a unique perspective on Chicago's eclectic and lively neighborhoods, operating pay-what-you-can walking tours throughout the year. The nonprofit, which was founded by Patti Swanson in 2016, is focused around giving local Chicago residents an opportunity to showcase their unique neighborhoods and cultural histories. Tours focus on a different Chicago neighborhood each month, lasting approximately two hours and ending at a local independent restaurant for a group meal. Past tour themes have included a Chicago History 101 tour series, urban planning tours, Jewish history tours, and tours focusing on the city's feminist and LGBTQ heroes. Though participants with financial limitations are absolutely encouraged to attend tours for free, donations are welcomed for those able to pay to help sustain continued business operations.

Phone: 512-757-7187, Email: chicagoforchicagoans@gmail.com, Website: website

8.Band of Bohemia

Band of Bohemia is a hip brewpub in Chicago's Ravenswood neighborhood, opened to the public in 2015 by Michael Carroll and Craig Sindelar. The brewpub is the first in the nation to receive the prestigious Michelin star designation as a gourmet dining destination, known for its unique global fusion fare, including Berkshire pork chops with kimchi and labneh, Old Bay-seasoned sweet breads served with Alabama-style white barbecue sauce, and brunch fare such as osetra caviar omelettes with brown butter crumble. Creative beers are rotated on tap, including variants such as the company's root beer stout, Lord of the Rings-themed "Rye of Sauron," and flagship Noble Raven Ale.

4710 N Ravenswood Ave, Chicago, IL 60640, Phone: 773-271-4710

9.Monk's Pub Chicago

Monk's Pub Chicago is an Old World-style pub and bar in Chicago's vibrant Loop district, originally opened by Mike Shaker in 1969 and moved to its current location in 1978. The kitschy bar is meant to evoke the vibe of a European inn pub, showcasing global artifacts from Shaker's travels from locations as far as Istanbul, Aruba, and Bali. An impressive beer list highlights up to 200 domestic, craft, and international import beers at any given time, including a daily-rotating selection of 16 regional independent brews on tap. Pub fare includes a delicious selection of meat, vegetarian, and vegan burgers, with gluten-free buns available upon request for diners with dietary concerns. Shareable appetizers are also served up, including unique takes such as tempura-battered cheese curds, loaded tater tots, and vegetarian mock buffalo wings crafted with cauliflower.

205 W Lake St, Chicago, IL 60606, Phone: 312-357-6665

10.The Randolph Street Market

The Randolph Street Market is an indoor-outdoor seasonal market held within Chicago's Beaux Arts Plumbers Hall, open to the public year-round inside the hall and showcasing outdoor vendors between May and September. The market, which has been acclaimed by international publications such as The New York Times, Travel and Leisure, and Lucky Magazine, is home to the internationally-renowned Chicago Antique Market, frequently described as a "mecca of cool" for perusing for the city's hippest and hottest market finds. More than 100 vendors are featured on site, including vendors selling as part of the Indie Designer Market and Modern Vintage Chicago. The family-friendly market also features a children's play area and activities for young visitors, including market treasure maps.

1341 W Randolph St, Chicago, IL 60607, Phone: 312-666-1200

11.Bobby's Bike Hike

Bobby's Bike Hike has been consistently ranked as Chicago's top sightseeing tour operation by TripAdvisor since its founding in 2002, earning accolades from major publications such as National Geographic and Midwest Living. The company offers one-of-a-kind bicycle, food, and walking tours of Chicago's distinct and diverse neighborhoods, hosted by experienced and friendly tour guides. All tours offer an insider's view on the city's architecture, history, and culture, with kid-friendly tours available for travelers exploring the city with children in tow. Discounted bike rentals are available for visitors looking to tour the city at their own pace, with partnerships offered for deals for city visitors attending events such as Lollapalooza or the Chicago Marathon and Triathlon.

Lake Shore Dr. & Ohio St., 540 N. Lake Shore Drive, Chicago, Illinois 60611, Phone: 312-245-9300

12.Merz Apothecary

Merz Apothecary was originally opened in 1875 by Swiss immigrant and Chicago pharmacist Peter Merz, housed within a drugstore facility in the city's North Side district. The famed apothecary, which is operated today by Anthony Qaiyum, developed a cult following throughout the 20th century and has been hailed by major celebrities such as Oprah Winfrey for its European-style herbal and homeopathic products. visitors can grab products crafted with ingredients such as tea tree oil, chamomile, and bitters, including products imported from European locales such as France and Sweden. Unique bath products are also sold, including soap handcrafted from Brazil nuts, along with a selection of name-brand products from companies such as Nivea.

4716 N Lincoln Ave, Chicago, IL 60625, Phone: 773-989-0900

13.Adler Planetarium

Adler Planetarium was the Western Hemisphere's first public planetarium facility at its opening in 1930, founded by Chicago entrepreneur Max Adler. The planetarium, which is located along the northeastern tip of Northerly Island within Chicago's Lake Michigan shorefront area, has been declared a National Historic Landmark and has received a gold medal from the American Institute of Architects for its renowned design by architect Ernest A. Grunsfeld, Jr. Three full-sized theaters are showcased at the planetarium, including the historic Atwood Sphere. The planetarium is also home to the Doane Observatory, one of the United States' only public urban research observatories. Visitors can dine at Galileo's Cafe or shop at the Adler Store, which sells a wide variety of educational toys, books, and games relating to science and astronomy topics. Museum exhibits are also showcased, focusing on the evolution of the universe and the history of America's space program.

1300 S Lake Shore Dr, Chicago, IL 60605, Phone: 312-922-782

14.BLVD

BLVD is a modern New American restaurant in Chicago's West Loop district, showcasing sophisticated cuisine and glamorous decor meant to evoke the golden era of Hollywood's Sunset Boulevard in the mid-2oth century. The two-story restaurant, which was opened in 2017 by married duo Kara and Frank Callero and their business partner Steve Zaleski, is decked out in lavish design elements, including crystal and gold decor pieces and a grand double staircase. A globally-inspired small plates menu draws from both classic American and post-WWII international cuisine influences, highlighting seafood towers, caviar platters, and classic housemade pasta dishes such as squid ink cavatelli and pork and seafood dumplings. Whole roasted fish and dry-aged steaks are also served up alongside a list of reinvented classic cocktails, fine wines, and regional independent beers on draft.

817 W Lake St, Chicago, IL 60607, Phone: 312-526-3116

15.Mi Tocaya Antojeria

Mi Tocaya Antojeria is a delightful Mexican restaurant offering from acclaimed executive chef Diana Dávila, a 2018 James Beard Award semifinalist. The restaurant, which is named for a Spanish term of endearment translating as "my namesake," is located within Chicago's historic Logan Square neighborhood and showcases beautiful Mexican-inspired art created by a number of Chicago-area independent artists. Diners can choose from a carefully-crafted selection of small and large plates that evoke Dávila's heritage and travels throughout Mexico, including lesser-known regional specialties and modern twists on old favorites. Unique entrees include smoked beer can chicken tacos, guisado de Nopalitos cactus stew, and caldo de res, prepared with short ribs, tongue, and bone marrow.

2800 W Logan Blvd, Chicago, IL 60647, Phone: 872-315-3947

16.Cruz Blanca

Cruz Blanca is a popular brewpub and small-batch brewery in Chicago's West Side district, opened in 2016 by Rick Bayless. The brewery, which takes its cues from Mexico City's classic 19th-century Cruz Blanca Brewery, focuses on ModMex-style lagers, along with a variety of tropical-inspired wild-fermented sour beers and IPAs meant for sipping along the beachfront during the summer. The restaurant's open-format kitchen produces authentic tacos filled with ingredients such as pork belly, árabe-style lamb, crispy shrimp, or grilled cauliflower, served up on a platter with wood-grilled onions and peppers for self-preparation. Large shareable Oaxacan-style tlayudas are also served, along with delicious appetizers such as chorizo queso fundido and asiago-jalapeno beer pretzels.

904 W Randolph St, Chicago, IL 60607, Phone: 312-733-1975

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17.HaiSous

HaiSous is one of Chicago's most unique restaurants, serving up authentic Vietnamese-style street food cuisine prepared by married duo Thai and Danielle Dang. The nationally-acclaimed restaurant, which was a finalist for the 2018 James Beard Award and earned a Michelin Bib Gourmand award the same year, showcases an outstanding menu of shareable plates, including fried chicken wings doused in caramelized fish sauce, prawn summer rolls with peanut-hoisin sauce, and fried whole fluke with Vietnamese herbs. Vegetarian entrees highlight unique meat substitutes and ingredients such as carrots, sweet potatoes, and daikon radishes. Next door, the restaurant's Cà Phê Dá cafe serves up a variety of Vietnamese-style coffees and espresso-based beverages, including vanilla egg custard lattes.

1800 S Carpenter St, Chicago, IL 60608, Phone: 312-702-1303

18.Spacca Napoli

Spacca Napoli is a casual, comforting Neapolitan-style restaurant opened in 2006 by Jonathan Goldsmith, serving up authentic Neapolitan thin-crust pizzas for more than a decade in Chicago's Ravenswood neighborhood. The restaurant, which crafts its own pizza dough daily and wood-fires its pizzas in a custom-crafted oven imported from Napoli, strives to recreate the robust market and cafe scene of Italy's Naples region, offering al fresco seating on its seasonal patio space during the warmer months. Delicious pizza flavors range from classic margherita variants to choices infused with toppings such as porcini mushrooms, Sardinian artichokes, and rapini, with gluten-free crusts available upon request for an additional charge. Classic Italian appetizers and desserts are also served up, alongside an extensive Italian wine menu.

1769 W Sunnyside Ave, Chicago, IL 60640, Phone: 773-878-2420

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19.Protein Bar and Kitchen

Protein Bar and Kitchen is one of Chicago's most popular restaurant chains, serving up health-conscious shakes, salads, scrambles, and superfood bowls in a quick-casual service atmosphere. Nutrition-packed dishes are available at breakfast, lunch, and dinner throughout the week, including high-protein salad choices, low-calorie wraps, and protein bowls served with ingredients such as sweet potato falafel, signature roasted tofu, and all-natural antibiotic-free chicken. Unique health-conscious "bar-ritos" are also offered, along with quinoa-infused oatmeal, breakfast scramble platters, and shakes with ingredients such as matcha tea, kale, collagen, and almond milk. 11 locations of the chain are offered throughout Chicago's neighborhoods, with locations also scattered throughout major cities such as Washington, D.C. and Denver.

235 S Franklin St, Chicago, IL 60606, Phone: 312-346-7300

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20.Oyster Bah

Oyster Bah is a charming New England-style seafood restaurant located in Chicago's Lincoln Park neighborhood, originally opened to the public in December of 2015. The bar, which is the sister restaurant to the city's popular Shaw's Crab House, serves up exceptional fresh seafood dishes throughout the week, including excellent seafood rolls, garlic shrimp platters, and clam chowder bowls available alongside grilled daily catches. Chilled seafood towers are also available for sharing, along with aloha mussels, jumbo shrimp cocktail, and Alaskan king crab legs. At the restaurant's Lettuce Entertain You bar, diners can enjoy fish sandwiches alongside an extensive selection of raw oysters, served up in a nautical-themed multi-level space.

1962 N. Halsted, 1st Floor, Chicago, IL 60614, Phone: 773-248-3000

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21.Mordecai

Mordecai is one of Chicago's newest and hottest restaurants, located within Wrigleyville's Hotel Zachary. The restaurant, which was opened by Matthias Merges in 2018 and is named after Chicago Cubs legend Mordecai Brown, is a perfect choice for diners looking to make a day out of a ball game trip to nearby Wrigley Field, serving up refined New American fare in a bi-level restaurant and cocktail bar space. Delicious shareable appetizers such as fried cheese curds are served up alongside high-class entrees such as squid ink arancini, roasted trout with yuzu emulsion, and herb-seasoned porchetta. Desserts play on classic stadium fare, including the restaurant's unique Crackerjack doughnuts, which are infused with caramel popcorn, crushed peanuts, and Bavarian cream.

3632 N Clark St, Chicago, IL 60613, Phone: 773-269-5410

22.ZED451

ZED451 is a delightful all-you-can-eat Brazilian restaurant in Chicago's Near Northside downtown district, opened in 2007 by Tavistock Restaurants. The one-of-a-kind concept restaurant showcases a menu of traditional Brazilian and South American fare at brunch and dinner service throughout the week, including fire-seared meat options such as picanha, linguica sausage, and herb-marinated leg of lamb delivered by chef servers. Buffet-style harvest tables offer build-your-own salad stations, charcuterie and cheese options, and traditional offerings such as roasted corn and barley salad or brussels sprouts and walnuts. All fare is made from scratch daily and available all-you-can-eat until diners ask chefs to stop service. An extensive cocktail menu features house-infused vodkas, while an international wine list offers selections to suit all price points. Seating areas range from an open kitchen counter and an intimate upstairs lounge to a seasonal outdoor rooftop deck serving up its own a la carte bar bites menu.

739 N Clark St, Chicago, IL 60654, Phone: 312- 266-6691

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23.The Magnificent Mile

The Magnificent Mile is one of Chicago's most famous landmarks, spanning 13 blocks along the city's North Michigan Avenue. As one of the United States' most acclaimed commercial districts, the Mile is home to a number of the nation's tallest record-breaking skyscrapers, including the John Hancock Center, which is home to the city's 360 Chicago observation deck. Throughout its rich century-long history, the district has become synonymous with high-end retailers such as Saks Fifth Avenue, Cartier, Burberry, and Ralph Lauren, attracting more than 22 million annual visitors to its retail options and public attractions. Luxury hotels, museums, and theaters also line the elite district, which was named as one of America's 10 Great Streets in 2007 by the American Planning Association.

625 North Michigan Avenue, Suite 401, Chicago, IL 60611, Phone: 312-409-5560

24.360 CHICAGO

360 CHICAGO is one of the city's highest public vantage points, located atop the iconic John Hancock Building in the city's high-end Magnificent Mile district. The observatory, which is located on the building's 94th floor over 1,000 feet above the city's Michigan Avenue, offers unparalleled 360-degree views of the city's beautiful skyline and Lake Michigan waterfront, originally opened in 1969 as the John Hancock Observatory. Adventurous tourists can enjoy the observatory's unique Tilt attraction, which featured tilted-glass window panes that moved 45 degrees outward for a truly unique scenic panorama. Visitors can also peruse the observatory's Chicago Multimedia exhibit or dine at Bar 94, the city's highest bar and lounge.

875 N Michigan Avenue, 94th Floor, Chicago, IL 60611, Phone: 888-875-8439