Top 10 Best Day Trips from Chicago

Nguyen Kieu Trang 9 0 Error

Are you looking for the best day trips from Chicago? Then you’ve come to the right place! When it comes to cities, Chicago has it all: stunning architecture, ... read more...

  1. Holland, Michigan is the perfect destination if you've been craving a vacation in Europe. Dutch immigrants first arrived in this small community on the eastern shores of Lake Michigan, nestled next to Lake Macatawa, in 1847. This vibrant heritage is still honored in the town today.

    The city's Windmill Island Gardens are a major draw, even though Holland's charming small-town atmosphere is enough to make it a destination worth visiting. An authentic Dutch windmill, a field of tulips, and a walk around canals can all be enjoyed here if you want to transport yourself to the Netherlands (open seasonally).

    Families can have a blast visiting Holland. If you have young children, take them to Nelis' Dutch Village so they can experience a unique version of the Netherlands. The park offers attractions like a petting farm, rides, and wooden shoe carving.

    Book in advance to avoid any hassles if you intend to travel during the renowned Tulip Time Festival, which takes place from May 7th to May 15th. Don't worry if you intend to visit at any other time of the year. Holland still has a lot to offer, including wonderful beaches, activities, and a main street brimming with eateries, boutiques, and breweries.

    • Need a Hotel? The Courtyard by Marriott Holland Downtown is a great option for where to stay in Chicago, since it’s within walking distance to downtown.
    • Distance from Chicago: 2.5 to 3 hours
    • Holland Website:

  2. The resort city of Lake Geneva is only one and a half hours northwest of Chicago. This kid-friendly community is located along Geneva Lake and provides visitors with the ideal mix of leisure time and outdoor pursuits. Take a stroll through Lake Geneva's downtown to experience some small-town charm while enjoying fantastic restaurants and a variety of local shops.

    The town also has a singular relationship to Chicago's past. Numerous affluent Chicagoans constructed sizable Gilded Age estates along the lake after the Great Chicago Fire of 1871. One of the town's top attractions, the Lake Geneva Shore Path, can be used to get to these estates by strolling along it. This 26-mile path offers lakefront views and the chance to get up close to the gilded mansions.

    You can take a wakeboarding private lesson at Gage Marine or rent a kayak or paddleboard from Clear Water Outdoor. When you're hungry, head to the town center's Egg Harbor Café and Simple Cafe for delectable, hassle-free diner fare. A popular champagne brunch with waterfront views is available at Baker House, a 19th-century mansion-turned-hotel, if you feel like spending some money.

    • Pro Tip: When walking along the Lake Geneva Shore Path, homeowners ask that guests be respectful and refrain from wandering up into their yards. The homes themselves are still private property.
    • Distance from Chicago: 1.5 hours
    • Lake Geneva Website:
  3. If you’re car-less, this small city is a perfect option for a day trip from Chicago. Hop on the Amtrak at Union Station and you’ll be in Michigan City in just over an hour. Or, take the South Shore Line and you can hop off right at the Indiana Dunes National Park, 15 miles of gorgeous sand dunes on the southern shore of Lake Michigan.

    Spend some time strolling around Washington Park and Beach in Michigan City. The park has a ton of family-friendly activities and is located on a section of Lake Michigan shoreline just outside of town. The Old Lighthouse Museum is a good choice if you're looking for something more engaging. In the warmer months, you can also go kayaking and taking boat tours on the lake.

    If you're hungry, head over to Shoreline Brewery, a hidden gem of a microbrewery with tasty pub fare and a changing menu of beers on tap. Fiddlehead offers high-quality comfort food, such as fried lake perch and grass-fed beef burgers, as well as a chance to experience regional flavors.

    • Did You Know? Washington Park is home to Indiana’s only working lighthouse.
    • Distance from Chicago: 1.25 hours
    • Michigan City Website:
  4. At first glance, you might not be familiar with South Bend, Indiana. But, chances are, you’ve heard of its nearby university: Notre Dame.

    Chicago and South Bend are separated by just over two hours. Start your day trip at the South Bend Farmer's Market for some shopping and a quick meal at the cafe (located in the center of the market). Spend an afternoon at the History Museum, a grand Victorian mansion that once housed the family of local entrepreneur and inventor James Oliver, to discover the city's cultural side. From there, peruse the local produce at the South Bend Farmers' Market, where you can buy everything from artisan breads and doughnuts to freshly picked fruits and vegetables. When you're hungry, go to Café Navarre, an elegant restaurant housed in a converted bank from the 1920s.

    Last but not least, a trip to South Bend wouldn't be complete without stopping by the stunning campus of Notre Dame. Explore the Basilica of the Sacred Heart, a magnificent Gothic-style church with frescoes and gold accents, to cap off your trip after seeing Notre Dame Stadium.

    • Pro Tip: Entry to the Basilica is free. If you’re wanting to see the inside of the church outside of mass hours, be sure to visit in the afternoon.
    • Distance from Chicago: 1.75 hours
    • South Bend Website:
  5. Falls probably don't come to mind when you think of Illinois. However, the town of Oglesby is located along the Illinois River, southwest of Chicago. With only a 5-minute drive separating Starved Rock State Park from Matthiessen State Park, this is the ideal starting point for outdoor enthusiasts to spend the day there.

    In the spring, go to Starved Rock State Park to see the canyon waterfalls that result from a lot of rain and melted snow. These hikes can be completed by anyone in reasonable shape in this family-friendly state park. There are a total of 18 canyons, 13 miles of trails, and a forest to explore at Starved Rock State Park.

    Visit Matthiessen State Park for some hiking trails, picnicking, and waterfalls that are a little more off the beaten path. There are calm trails in this state park, interesting geological features to see, and a wide variety of plants and animals.

    After your outdoor adventures, unwind with a treat from the past at The Rootbeer Stand or visit Ottawa's nearby "farm to foam" Tangled Roots Brewery and Lone Buffalo Brewpub. This is one of the best day trips from Chicago for some outdoor adventure and fresh air.

    • Did You Know? Starved Rock State Park is actually one of the best places in the country to see Bald Eagles.
    • Distance from Chicago: 2 hours
    • Oglesby Website:
  6. A 385-acre garden brimming with countless kinds of flowers and luxuriant vegetation, the Chicago Botanic Garden. Walks through the natural areas or themed, landscaped gardens are enjoyable for visitors of all ages. Ample benches are available for visitors to use as they see fit along the walkways. Those who prefer to ride through the well-known gardens or are unable to walk can also use the tram, which is also available.

    The best activity is to simply take a stroll through the various landscapes that have been crafted here and admire the magnificent plant and animal life. But there are also some excellent workshops and other activities. Admission is completely free, although parking is expensive.

    The quickest method of transportation to the Chicago Botanic Garden is by car. However, there is also public transportation from Chicago's downtown. The garden is available for your enjoyment every day of the year. Just be aware that season can affect hours.

    • Pro Tip: Purchase tickets online and in advance to get the best pricing. The website will also have you choose a specific time slot.
    • Distance from Chicago: 30 minutes
    • Chicago Botanic Garden Website:
  7. The Oak Park neighborhood is located about 9 miles west of Chicago's downtown Loop. The residences of two legendary American figures—famous architect Frank Lloyd Wright and significant author Ernest Hemingway—are what make this historic neighborhood most famous.

    Frank Lloyd Wright's home and studio, as well as a few other Prairie-style homes he created, are located in Oak Park, so you can't claim to be a fan of his work until you've spent the day there. Make a reservation for a tour with the Frank Lloyd Wright Trust if it's your first time. This nearby city neighborhood is one of the best day trips from Chicago for art and architecture enthusiasts.

    If you are hungry, stop by Maya del Sol for brunch or dinner, where the ceviche is top-notch and the margaritas flow like water. Excellent dining options, retail stores, and cultural venues can be found in downtown Oak Park. Take a seat at Kinslahger Brewing Company, a small but mighty taproom serving lagered brews, if you have time for one more stop.

    • Pro Tip: If you’re coming from Chicago and want to take the “L,” take the Blue Line headed for Forest Park and get off at the Austin stop. This is an hour-long train ride, but a good way to get some extra sightseeing in while you’re at it.
    • Distance from Chicago: 30 minutes
    • Oak Park Website:
  8. Top 8


    The town of Galena is located in northwest Illinois, only three hours from Chicago. It is simple to understand why this location frequently appears on lists of the "best small towns in America" due to its historic sites and small-town charm. Galena is a wonderful destination for families and couples seeking a small-town, romantic getaway when it comes to day trips from Chicago.

    Although this Mississippi River city's resorts may be its claim to fame, you don't have to stay the night to take advantage of its assortment of historical sites and outdoor pursuits. Otto's Place serves brunch where you can start your day with biscuits and gravy made with in-house buttermilk biscuits and locally sourced sausage while sipping on a bloody mary or mimosa. To ride along the trails and into town, cross the Galena River to Nuts Outdoors and rent an electric bike.

    Visit the Ulysses S. Grant Home, which was given to the 18th president as a gift after his service in the Civil War and is the city's most renowned landmark. The Galena & U.S. Grant Museum, which also has an off-site operational blacksmith shop, is where you can find out more information. This history is also on display at Galena Brewing Company, where you can enjoy a beer brat with sauerkraut and housemade mustard while sipping Ult's Dark oatmeal stout and listening to live music.

    • Pro Tip: Miss Kitty’s Grape Escape is a local favorite for drinks, live music, and all-around good vibes.
    • Distance from Chicago: 3 hours
    • Galena Website:
  9. New Glarus is one of the most interesting day trips from Chicago for visitors of all ages. This charming Wisconsin town, now referred to as "America's little Switzerland," was originally given its name after Glarus, Switzerland.

    You'll have a Swiss experience with a touch of the Midwest in New Glarus. There is a lot of Swiss history in the town center. There are two museums, specialty stores, and chalet-style structures. The town also hosts Swiss celebrations and events all year long. Visit during the New Glarus Oktoberfest in late September, the Wilhelm Tell Festival in early September, or the New Glarus Christkindl Market in early December for that extra touch of Switzerland.

    For a taste of Switzerland, you can head to the Chalet Landhaus Restaurant or Glarner Stube. The Swiss Historical Village Museum is another great place to immerse yourself in the town’s unique history. For beer aficionados, be sure to check out New Glarus Brewing Co. for a taste of its famous Spotted Cow beer.

    • Need a Hotel? Book the Fairfield Inn & Suites by Marriott Madison Verona for a comfortable stay with modern amenities. Or check out Nilani’s guide to staying in Chicago for more accommodation suggestions.
    • Distance from Chicago: 2.75 to 3 hours
    • New Glarus Website:
  10. Nature lovers can get ready for one of the best day trips from Chicago. Door County, located on a peninsula outside of Green Bay, Wisconsin, is a county made up of more than 10 small towns. The region is well-known for its pristine scenery, parks, and wide variety of outdoor pursuits. Even though a trip to Door County can be completed in a single day, a long weekend is the ideal length of time to spend there.

    One of Door County's top attractions is cherry blossom season, which you can experience by segwaying through groves of trees with white blossoms. These are best seen while zipping through the air, highlighting the craggy rock formations, distinct stone cliffs, and turquoise, calm waters. There isn't a better way to take in more scenery than to sip wine in a vineyard.

    There are 8 wineries nearby where you can unwind, create lasting memories, and enjoy the sunshine. In this county, there are 11 lighthouses, some of which are more visible than others. Peninsula State Park is a highlight of Door County with its hikes through the unique terrain and lakeshore views of the clear water perfect for a friendly rock-skipping competition.

    • Need a Hotel? The town of Sturgeon Bay is a great landing spot for other Door County activities. For a homey feel and touch of history, stay at the Scofield House B&B. Looking for a little more privacy? The Westwood Shores Waterfront Resort offers suite accommodations and lakefront views.
    • Distance from Chicago: 3.75 to 4 hours
    • Door County Website:

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