The third most populous city in the entire United States, Chicago is the biggest city in Illinois and home to close to 10 million people in its full metropolitan area. It's a vibrant city with a lot to offer, especially in terms of entertainment. There are many bars, comedy clubs, live music venues, and more to be found around Chicago, so it's no surprise that millions of people choose to visit the Windy City each and every year.

Chicago is also nicely placed for a number of day trips, being connected to some beautiful locations by train. So if you're living in Chicago or visiting the city and looking to spend a day somewhere different, here are some of the best day trips you can take from Chicago by train. CDC information for travelers. Hours/availability may have changed.


1.Day Trip from Chicago to Milwaukee

Day Trip from Chicago to Milwaukee
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Milwaukee is less than two hours away from Chicago by Amtrak and it's one of the best places you can choose for your day trip. Yes, it's a big city location just like Chicago, but it's a very different kind of place. There are plenty of unique experiences to be had in Milwaukee, and the pace of life is a little slower and more subdued than the Windy City's.

Popular things to do in Milwaukee include visiting the Art Museum and the Harley-Davidson Museum. A trip to the Mitchell Park Horticultural Conservatory is always worth one's time as well, and a walk along the side of the Menomonee River is particularly enjoyable for families and couples alike.

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2.Day Trip from Chicago to Oak Park

Day Trip from Chicago to Oak Park
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Oak Park is one of the closest locations to Chicago for a day trip. In fact, you can get to Oak Park by train in about 40 minutes, so it's a great spot to choose for people who don't really like long journeys or don't want to have to get up really early just to make the most of their day.

Best known as the home of famed architect Frank Lloyd Wright, Oak Park is a really pretty place with a lot to offer. You can enjoy a full Frank Lloyd Wright tour, visiting the architect's former home and studio, as well as passing by some of the beautiful houses he helped create. There are some quality craft beer bars and decent restaurants to be found in Oak Park as well, so it's great for a relaxing day out.

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3.Day Trip to Michigan City from Chicago

Day Trip to Michigan City from Chicago
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The journey from Chicago to Michigan City takes a little over an hour by Amtrak, and it's well worth the trip. This unique city sits on the south shore of Lake Michigan, so it's one of the best options for anyone seeking a Great Lakes day trip outside of Chicago. You can get direct Amtrak trains from Union Station to Michigan City, and the journey is quite scenic and picturesque.

Once you arrive at Michigan City, you can explore and experience some of the various attractions like Washington Park Zoo, the Old Lighthouse Museum, and the always-impressive Barker Mansion. Otherwise, if you're just in the city to lie back and relax, you can head down to the beach and admire the amazing views all around you.

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4.Kalamazoo from Chicago

Kalamazoo from Chicago
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Head over the state line into Michigan for a day trip to Kalamazoo. You can take the Amtrak to this beautiful, artistic city, with the journey taking around two hours in total. There are several daily trains running right to Kalamazoo, leaving early in the morning and setting back late in the evening, so the timings are always right for a day trip.

Kalamazoo is a very inspiring place that holds a lot of appeal for poets, artists, and other creative people. It's also home to some interesting attractions including the Air Zoo aircraft museum, the Kalamazoo Valley Museum, and the Gilmore Car Museum. It's also a great spot for foodies, home to some of the best restaurants and bars in Michigan, with plenty of local craft breweries to visit too.

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5.Day Trip to Libertyville from Chicago

Day Trip to Libertyville from Chicago
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Another popular day trip option from Chicago by train, Libertyville is a small village in Lake County, Illinois. It's a charming place with very friendly locals, offering a great escape from the big city streets. The journey from Chicago to Libertyville by train only takes about an hour in total.

You won't find too many major attractions or monuments in Libertyville, but it's a lovely location for those who just want a calm and pleasant day out of the city. There are some super bars and restaurants here, as well as a great range of boutiques and small stores. The local movie theater is quite a popular hangout spot too.

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5 Best Day Trips From Chicago By Train



More Ideas: Harvey House Bed & Breakfast

Harvey House Bed & Breakfast is a charming bed and breakfast inn located in Oak Park, IL, just a few miles from the heart of downtown Chicago. Set within easy walking distance of outstanding restaurants, trendy boutiques and several museums and galleries, Harvey House is a perfect getaway for this wanting to explore Chicago. Boasting comfortable accommodations in the form of five luxurious guest suites, upscale amenities, and facilities and gracious, welcoming hospitality, Harvey House Bed & Breakfast promises an unforgettable stay.

Harvey House Bed & Breakfast offers five luxurious appointed and individually decorated guest suites with elegant country-style décor and plush furnishings, and private en-suite bathrooms with walk-in showers, whirlpool tubs, thick towels, bathrobes and slippers, and Aveda bath products. Sitting areas have cozy fireplaces, comfy seating and modern amenities include central air-conditioning, mini fridges, hairdryers, flat screen televisions with cable channels, DVD players, irons and iron boards, CD players, and complimentary wireless Internet access.

The Jimmy Stewart Suite is a grand king suite with a king-size bed in deluxe linens, an en-suite bathroom with a double whirlpool tub, walk-in shower, bathrobes and slippers, and Aveda bath products. A spacious sitting area has an oversized chaise lounge for two, antique furniture, a hand stenciled carpet, and an inlaid writing table.

The Garden Suite has a king-size bed with deluxe linens, an en-suite bathroom with a double whirlpool tub, walk-in shower, bathrobes and slippers, and Aveda bath products. A spacious sitting area has a three-sided fireplace, comfortable seating, antique furniture, and lovely views of the garden.

The Queen Fireplace Suite is decorated in rich textures and deep sensual colors with touches of Asian flair and features a corner fireplace, a flat screen television, a king-size bed with deluxe linens, an en-suite bathroom with a soaking tub, walk-in shower, bathrobes and slippers, and Aveda bath products.

The Chalet Suite features sloping bead board ceilings, cherry wood hardwood floors, antique furniture, a fully equipped kitchenette, and a massive fieldstone fireplace. The suite has a solid walnut king-size bed in deluxe linens, and an en-suite bathroom with a whirlpool tub, walk-in shower, bathrobes and slippers, and Aveda bath products.

The Oak Park Suite is a large, deluxe king suite with cherry hardwood floors and furniture, a spacious sitting area with a leather couch and writing desk, a fully equipped kitchenette with granite countertops, and an en-suite bathroom with a rain shower, bathrobes and slippers, and Aveda bath products.

A delicious gourmet breakfast is served every morning and includes fresh fruit platters, French toast, oven pancakes, freshly baked goods, and specialty entrées, as well as hot coffee, tea, and fresh fruit juices.

Amenities at the Harvey House Bed & Breakfast include a gourmet breakfast served in the dining room every morning, and luxurious accommodations with central air-conditioning, whirlpool tubs, and fireplaces.

Located in Oak Park, the Harvey House Bed & Breakfast is within proximity to many attractions and activities that can be enjoyed in the Oak Park area, which is home to the Frank Lloyd Wright Home & Studio, the Ernest Hemingway Museum, the Brookfield Zoo and more. Other attractions include the Ernest Hemingway Birthplace, the Cernan Earth, and Space Center of Triton College, the Escape Factor, and Frank Lloyd Wright's Unity Temple. Don’t miss visiting Frederick Law Olmsted Society of Riverside, the Garfield Park Conservatory, and Historical Society of Oak Park and River Forest, Oak Park Conservatory, Wonder Works Children's Museum, and the Quincy Street Distillery.

Back to: Romantic Weekend Getaways in IL

107 South Scoville Avenue, Oak Park, Illinois, IL 60302, Phone: 708-848-6810

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More Ideas: Bishops Hall Bed & Breakfast

Located in the historic district of Oak Park in Illinois, Bishops Hall is an elegant bed and breakfast designed and decorated in the gracious Georgian style. Built in 1916 and constructed in the Georgian Revival style, the beautifully maintained red brick building served as the residence of the bishop of the Orthodox Church, culminating in its namesake.

Bishops Hall features three distinctive and individually decorated guest rooms with elegant décor in the Georgian style and modern conveniences. All three guest rooms have queen-sized four-poster beds with plush linens and down pillows and comforters, and private bathrooms. A full breakfast is served in several different rooms in the guest house from the cozy breakfast room in the winter months on the lovely outdoor terrace in the summer.

Bishops Hall is ideally located in the heart of the Oak Park historic district and is within walking distance of several of the village’s most famous attractions. A short stroll takes you to Earnest Hemmingway’s birthplace, the Frank Lloyd Wright Home and Studio, and the shops and restaurants of downtown Oak Park. The Hall is just 15 minutes’ away from The Art Institute of Chicago, the Navy Pier, and Chicago’s Magnificent Mile.

Bishops Hall features three distinctive and individually decorated guest rooms with elegant décor in the Georgian style and modern conveniences such as plush bathrobes, organic bath products, hairdryers and complimentary fresh flowers and chocolates.

The Coral & Blue Room is a spacious master suite with 950 square feet. It features a large bedroom with a king-size four-poster bed dressed in imported linens, and an en-suite bathroom with a marble shower and steam room and antique ball-and-claw tub, plush towels and robes and organic bath products. The suite also has a separate dressing area, several seating and lounge areas, a fireplace and beautiful views of expansive windows. Modern conveniences include hair dryers and complimentary fresh flowers and chocolates.

The Tartan Room is 550 square feet in size and features a bedroom with a king-size four-poster bed dressed in imported linens, separate dressing room, and en-suite bathroom with marble bath and shower combination, plush towels and robes and organic bath products. This junior suite also has a private balcony that overlooks the garden terrace. Modern conveniences include hair dryers and complimentary fresh flowers and chocolates.

The Yellow Room is a cozy retreat at 250 square feet with a queen-size four-poster bed dressed in imported linens and a private bathroom with a bathtub and European hand shower, plush towels and robes and organic bath products. Modern conveniences include hair dryers and complimentary fresh flowers and chocolates.

A full breakfast is served in several different rooms in the guest house from the cozy breakfast room in the winter months on the lovely outdoor terrace in the summer.

Amenities at Bishops Hall include a delicious complimentary continental breakfast served on the terrace in summer and in the dining room in winter, an elegant and comfortable communal living area in which to relax and a beautifully manicured garden.

Bishops Hall is ideally located in the heart of the Oak Park historic district and is within walking distance of several of the village’s most famous attractions. A short stroll takes you to Earnest Hemmingway’s birthplace, the Frank Lloyd Wright Home and Studio, and the shops and restaurants of downtown Oak Park. The Hall is just 15 minutes’ away from The Art Institute of Chicago, the Navy Pier, and Chicago’s Magnificent Mile.

Back to: Weekend Getaways from Chicago

605 Iowa Street, Oak Park, Illinois 60302, Phone: 708-383-7774

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