Chicago Chicago Moving Guide

The Best Weekend Trips from Chicago

Chicago skyline
Written by Lily Rogers

Chicago is a fantastic city with so much to see and do that you can spend years here and not get to it all. That doesn't mean residents and visitors alike don't want to explore the wider surrounding area, however. Another perk to Chicago is there are so many awesome day trip options, you're spoiled for choice.

Whether you can only spare a day or are looking for a long weekend getaway, possibilities are abundant within hours by train or by car. Here are our picks for the best weekend trips from Chicago.

1-day trips from Chicago

Starved Rock State Park, Oglesby, Illinois

93-mile drive

Starved Rock state park waterfalls
Image via Jason Patrick Ross/Shutterstock.com

Breathe deep and get meditative in this lush, forested park with rushing waterfalls. It's a roomy place for your dog to run and play, and what's better than watching dogs get excited by nature? This is one of the best dog-friendly day trips from Chicago, and most of the spots listed on our itinerary welcome your four-legged friend. With no entrance fees, Starved Rock is ideal for the budget-conscious, too.

Day Itinerary

  • Mid-morning: Before witnessing the calm majesty of Starved Rock waterfalls, stop for breakfast (and a pup-accino for Fido) in North Utica at Nonie's Bakery & Cafe just north of the park.
  • Late morning: Take your pup for a hike on the 13 miles of trails at Starved Rock State Park.
  • Afternoon: Visit the largest two-sided fireplace in Illinois at the Starved Rock Lodge. And bring your best friend—dogs are allowed on the veranda at the Back Door Lounge.
  • Late afternoon: Stop in for a sweet treat at The Rootbeer Stand in Oglesby for classic drive-thru floats. Dogs with their heads out the window are welcome, of course.
  • Evening: If you're rolling dog-free, reward yourself with a tasting at August Hill Winery in North Utica. It's open until 8 p.m., so you can take your time and sip responsibly.

Lake Forest, Illinois

30-mile drive or 1-hour train ride

Lake Forest IL lakefront
Image via Jennifer H./Yelp

Lake Forest is very easy to get to without a car and is walkable once you're there, making it an excellent contender for best day trips from Chicago by train. If you choose to drive, it's a quick trip and you can make the most of your time.

Day Itinerary

  • Morning: The train drops you right in charming Market Square, where you can wander, window shop, and stop in for a morning bite at Egg Harbor Café a little to the south. 
  • Late morning: Stroll 1 mile along Deerpath Road to get to Forest Park Beach. Take to the water when you rent a kayak or paddleboard with Lake Forest Sailing.
  • Evening: Treat yourself to dinner and a show. MLG Restaurant is one of the best in town, and Center Stage theater features classic productions like The Importance of Being Earnest.

Greater St. Charles, Illinois

45-mile drive or 1.5-hour train ride to Elburn

St Charles IL riverfront
Image via joe arrigo/Shutterstock.com

While you can take the train to this area, it may be more convenient to have a car, because there's a lot to explore. From outdoor spaces to food markets, this is one of the best places to travel from Chicago for foodies and nature lovers.

Day Itinerary

  • Morning: Heritage Prairie Farm in Elburn is an in-season must, where you can buy local products and organic produce at the farm store and charge up for the day with their signature honey latte.
  • Midday: Head into St. Charles and picnic on your new market goods in Pottawatomie Park overlooking the Fox River. Then take a St. Charles Paddlewheel Riverboats tour to take in all the sights.
  • Afternoon: Explore the Main Street and Riverside Avenue area and snap some pictures of the historic Arcada Theatre.
  • Evening: Round out a wonderful day with a splendid farm-to-table dinner at The Finery & Blacksmith Bar.

2-day trips from Chicago

Kalamazoo, Michigan

145-mile drive or 3-hour train ride

Milham Park in Kalamazoo MI
Image via Thomas Leo Schillaci Jr/Shutterstock.com

Kalamazoo is crunchy, artsy, sudsy (of the beer variety), and friendly. There's much to see and do, so stay overnight to pack your trip as tight as you can and sample all the goods. To get here without a car, you can take the Amtrak Blue Water train from Union Station to Kalamazoo.

Day 1 Itinerary

  • Late morning: Within walking distance from the train, and with affordable parking options, Kalamazoo Valley Museum offers free admission and is a great way to get acquainted with the city's cultural side.
  • Afternoon: Kalamazoo has put itself on the map in the beer community, making it one of the best weekend trips from Chicago if you're a fan of the hops and barley.
    • Start your beer tour at Arcadia Brewing Co. to sample their seasonal, specialty, and year-round winners.
    • Famous Bell's Brewery is a must-stop, with tours every hour from noon to 5 p.m. on Saturdays, and an on-site restaurant when you're ready for lunch.
    • Self-described nano-brewery Tibbs Brewing specializes in delicious small-batch brews.
  • Evening: If you haven't had enough of the golden stuff, dine at Rustica, which does craft beer pairings and serves inviting dishes made with local ingredients.
  • Night: Settle in for the night at the warm and comfy Kalamazoo House Bed & Breakfast.

Day 2 Itinerary

  • Morning: Your train leaves at 1:30 p.m., but that's still enough time to brunch it up at Fuze Kitchen & Bar with carafes of mimosa or sangria.
  • Late morning: Be active with a bike rental from PEDAL and ride along Mayors Riverfront Park or take a leisurely stroll through idyllic Milham Park.

South Bend, Indiana

90-mile drive or 2.5-hour train ride

Notre Dame in South Bend IN
Image via RebeccaDLev/Shutterstock.com

Rich history, arts and culture, and emerging food gems await you in South Bend, making it one of the better weekend getaways near Chicago. No wheels? No problem. You can get here on the South Shore Line, then ride share around town.

Day 1 Itinerary

  • Afternoon: Wander the Notre Dame campus—its beautiful architecture and landscaped grounds are full of magnificent exploration.
  • Evening: Dine on French cuisine at Sorin's in the Morris Inn before getting comfortable for the night at the modern boutique hotel Inn at St. Mary's.

Day 2 Itinerary

  • Morning: Start your day at Luisa's Café for a full sit-down breakfast or to grab a pastry and coffee from the bakery.
  • Late morning: Learn about the area's history—from fashion to culture to architecture—at The History Museum
  • Afternoon: Swing by the Oliver Mansion to tour an example of opulent 19th-century South Bend living.
  • Late afternoon: Have a late lunch at South Bend Brew Werks, where the satiating menu includes flatbreads, grilled cheeses, and baked pastas.
  • Evening: Add crescendo to your day by taking in a show at Morris Performing Arts Center before calling it quits for the night. If you took the train, you'll leave bright and early tomorrow and be back in Chicago by 9 a.m.

Fennville, Michigan

140-mile drive

Cranes Pie Pantry in Fennville MI
Image via James J./Yelp

Surrounded by abundant agriculture and blessed with a nostalgic quaintness, Fennville is quintessential Americana. Relaxed and pleasing, Fennville checks off all the boxes for getting away from city chaos. There's no direct train route, but you can take a 3-hour train from Chicago Union Station to Holland, then car-share your way 15 miles to Fennville.

Day 1 Itinerary

  • Midday: Hungry after your journey? Crane's Pie Pantry serves burgers, hard ciders, and pies, of course! (They even have a four-choice pie flight.)
  • Afternoon: Go treasure hunting at Featherstone Antique Mall, where you can find everything from furniture to jewelry.
  • Evening: Take in the sunset from the gazebo overlooking Lake Michigan at West Side Park, then seek refreshment at Waypost Brewing Co.
  • Night: Call it a day at the pretty-as-a-picture B&B, The Kingsley House.  

Day 2 Itinerary

  • Early morning: Take a morning stroll down the beach at Pier Cove Park.
  • Late morning: Get local at Crane Orchards for u-pick fruit or take on the 20-acre corn maze.
  • Midday: Lunch at eatery and bakery Salt of the Earth, and do not leave without fresh baked bread to take home.
  • Evening (for drivers): Drive part of the Allegan County Heritage Trail for scenic area views before heading home.

3-day trips from Chicago

Wisconsin Dells, Wisconsin

195-mile drive or 3.5-hour train ride

Wisconsin Dells boat trip
Image via Nina H./Yelp

If you're searching for the best day trips from Chicago for families, look no further than the Dells (although you'll want to spend more than a day here). No driving, either: Take the Amtrak Empire Builder train from Union Station. The kids will be having so much fun, they'll forget to argue. No kids? Don't worry—there's plenty to appeal to older tastes, too. Wisconsin Dells is flexible like that.

Day 1 Itinerary

The train gets in around 6 p.m., and it's about a 4-hour drive, so Day 1 is mostly about getting here and settling in.

  • Upon arrival: Great Wolf Lodge is built for kids, with bunk beds, cartoon murals, and activities like story time and PJ parties. For adults, Sundara Inn & Spa is a serene resort in a pine forest setting.
  • Evening: Pick up the best cheese ever at Carr Valley Cheese Co., indulge at Swiss Maid Fudge, and grab a bottle of wine for a grown-up snack before bed. Or, take the kids to Goody Goody Gum Drop Candy and Oodlesmack Popcorn before running it off on an interactive scavenger hunt at Wizard Quest.

Day 2 Itinerary: Wisconsin Dells for Families

This isn't the Water Park Capital of the World for nothing. It's what makes this one of the best trips from Chicago in the summer, and a must-do at least once.

  • Morning: Family recipes and a family-friendly environment make Mr. Pancake a go-to favorite for diners with kids in tow.
  • Midday: Memorial Day through Labor Day, the park to visit is Noah's Ark Water Park, the biggest in America. Mount Olympus also should not be missed, and the theme park and water park are open year-round.
  • Evening: Even after along day in the sun, the kids will love Buffalo Phil's Pizza and Grille, with its Western décor and model train that runs throughout the restaurant.

Day 2 Itinerary: Wisconsin Dells for Adults

Wisconsin Dells isn't only known for its man-made wonders. Its incredible natural landscapes and wineries make it a great weekend getaway near Chicago for couples.

  • Morning: Grab a gourmet waffle sandwich and an espresso from Belgiis Waffle Bar. Take your pick of sweet and savory options.
  • Late morning: Take a cruise with Dells Boat Tours to see the area's nature side as you ride past corrugated rocks and tree-topped cliff faces.
  • Afternoon: Visit nearby Wollersheim Winery for an afternoon of scenic tastings.
  • Evening: Continue your relaxed day with dinner at High Rock Café, where you're met with fresh seasonal plates and friendly service.

Day 3 Itinerary

You'll probably want to get on the road early, and the train leaves at noon, but you still have time to…

  • Morning:At any age, taking selfies with deer is a magical experience, and Wisconsin Deer Park is the best place to realize this dream.
  • Late morning: Have one last adventure when you hit the bumper boats at Timber Falls Adventure Park.

Indianapolis, Indiana

185-mile drive or 5-hour train ride

Indianapolis Indiana skyline
Image via f11photo/Shutterstock.com

Indianapolis perhaps merits more than a last-minute weekend getaway from Chicago, but who says you have to go just once? We recommend exploring as often as your schedule allows. 

Day 1 Itinerary

  • Afternoon: Stretch your legs and explore the Canal and White River State Park while enjoying views of the downtown skyline.
  • Late afternoon: Get homey in a Mint House apartment downtown, and enjoy an aperitif at Libertine Liquor Bar
  • Evening: Walk a few blocks up to Livery for Latin American flavors in a chic setting.

Day 2 Itinerary

  • Morning: Get a fresh start on the day at Garden Table, where cold-pressed juices, grain- and produce-heavy fare, and light yet delicious flavors come standard.
  • Late morning: Get acquainted with the city on a trip with Indy Fun Trolley Tours.
  • Midday: Seek thought-provoking art and sprawling, manicured grounds at Newfields (The Indianapolis Museum of Art). Alternatively, enjoy racing history at the Indianapolis Motor Speedway Museum.
  • Late afternoon: Peruse the stalls at Indianapolis City Market and enjoy the bustling atmosphere and plentiful snacks, from Middle Eastern bites to pizza by the slice.
  • Evening: Hire a gondolier for a sunset cruise along the canal before tucking into a delicious meal at Bluebeard.

Day 3 Itinerary

  • Morning: Breakfast at Milktooth will set you up for the day with creative plates like sourdough pearl sugar waffles and sour cream biscuits with curry butter and pomegranate molasses.  
  • Midday: Hit up the Broad Ripple neighborhood to shop and explore on your way out of town. At shops like Plenty LifestyleIndy Arts Vintage & Marketplace, and Books & Brews, you'll find the perfect keepsake to remind you of your stay.

Whether you're moving to the city or are in the area for an extended vacation, you will be amazed at all the diverse things to see near Chicago. So pack up your overnight bags and jump in the car—or on the train. You've got places to be!

Header image via marchello74/Shutterstock.com

About the author

Lily Rogers

Lily is a writer, editor, and content strategist. Her curiosity spans genre, from travel to pop culture to food, and she writes about all that and more. She's also a social introvert, literature nerd, and (slight) hoarder. When not in pursuit of her next adventure, she's most likely at home with her wife and two cats.

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