Chicago has some of the most impressive attractions, delicious food, fun nightlife, and awe-inspiring skyscrapers in the Midwest. So why would you want to leave? Well, the big city life can get exhausting and locals may need a little break from the hustle and bustle of the Windy City. Plan a day trip out of Chicago to get a much-needed breath of fresh air with a group of friends or family. Even if you’re planning an outing with work colleagues or a school field trip, organizing a day out of town is a wonderful way to team-build and learn.

A road sign at the beginning of Route 66

Traveling Around the Midwest with a Group

Deciding where you’ll go is only the first step in your journey. You’ll also need to figure out how to get your group to, from, and around your destination. Small groups can easily pack everyone into a car or even build a caravan if needed. But if you’re traveling with a large group, you’ll need a more spacious way to get around. That’s where GOGO Charters comes in with a Chicago charter bus rental.

Book a charter bus rental in Chicago and keep anyone from having to sacrifice the mileage on their personal vehicles or feeling uncomfortable while stuck in a small car. A motorcoach rental will give your group plenty of space to relax on the road while a professional driver gets you where you need to be! Call (312) 546-3925 to get a quote on a minibus or charter bus outfitted with WiFi, TVs with DVD players, and reclining seats for a smooth and easy ride to these nearby cities:

1.   Gurnee, IL

Distance from Chicago: 50 minutes or ~40 miles

Gurnee isn’t all too far from Chicago, and it’s the perfect place for thrill-seekers or groups with kids to spend an afternoon. This small town is home to Six Flags Great America and the Great Wolf Lodge Water Park, which offer hours upon hours of family-friendly fun just a little ways from the big city. Enjoy rides on the world’s fastest wooden roller coaster at Six Flags or cool off in the wave pool at Great Wolf Lodge.

However, note that both parks see large attendance and may not be the best places to avoid big crowds. So if you’re traveling during peak times like summer, be sure to practice patience, as wait times can get long. Once you finish enjoying the rides, stretch out and relax in your charter bus on the way back to Chi-town.

Two women laughing and riding a wooden rollercoaster

Six Flags Great America

Highlights: Goliath, Raging Bull, and American Eagle roller coasters, Batman-themed rides, Hurricane Harbor (seasonal)

Address: 1 Great America Parkway, Gurnee, IL 60031
Phone: (847) 249-1776

Great Wolf Lodge Water Park

Highlights: lazy river, wave pool, ropes course

Address: 1700 Nations Dr, Gurnee, IL 60031
Phone: (844) 482-9653

Charter bus travel tip: Gurnee’s theme parks are used to handling a large number of vehicles and motorcoach parking can be organized easily. Charter bus parking at Six Flags is $30, and your driver will get free admission when they present a valid CDL license. Great Wolf Lodge offers oversized vehicle parking with purchases of day passes.

2.   Milwaukee, WI

Distance from Chicago: 1.5 hours or ~93 miles

Some may consider Chicago the cultural hub of the Midwest, but nearby Milwaukee has a lot to offer too. The city has a long history as well as several historic districts and unique attractions to visit on a day trip. Groups of beer lovers can explore the city’s historic breweries,  like Pabst Brewing Company and Miller Brewing Company. These century-old establishments offer tours and tastings sure to intrigue those who love a good brew.

If you’re traveling with underage visitors, don’t worry — Milwaukee has plenty for them as well. Take a tour of the undeniably cool Harley-Davidson Museum, catch a Brewers game at Miller Park, or grab tasty local bites at the Milwaukee Public Market. One of the best times for Chicagoans to visit Milwaukee is during a Cubs vs. Brewers game! Book a charter bus for your Cubs fan club and ride from Chicago to Milwaukee for the big match.

The inside of Miller Park, home of the Milwaukee Brewers.
The inside of Miller Park, home of the Milwaukee Brewers. Image credit: Bryce Edwards on Flickr.

Harley-Davidson Museum

Highlights: Engine room exhibit, Bike Night Thursdays

Address: 400 W Canal St, Milwaukee, WI 53201
Phone: (414) 287-2789

Miller Park

Highlights: retractable roof during games, game day tours, iconic sausage horse races

Address: 41 Brewers Way, Milwaukee, WI 53214
Phone: (414) 902-4452

Milwaukee Public Market

Highlights: fresh seafood vendors, local baked goods, wine bar

Address: 1400 N Water St, Milwaukee, WI 53202
Phone: (414) 336-1111

Charter bus travel tip: Oversized parking can be found at most major attractions like Miller Park. Be sure to organize parking for your charter bus at each stop on your itinerary or find a lot that offers in and out privileges throughout the day.

3.   Lake Geneva, WI

Distance from Chicago: 1.5 hours or ~90 miles

Looking for a quiet, calm place to dip your toes in the water? The Chicago area has beautiful lakefront beaches if you want a day to soak up the sun, but they can get quite crowded, making it a pain to find space for your group to spread out and relax. Instead, shuttle up to Lake Geneva in Wisconsin for a lovely day in the sun.

Pack your charter bus’s luggage bays with all your water gear and ride to Lake Geneva Public Beach, Big Foot Beach State Park, or Fontana Beach. The area around the lake also includes local restaurants, resorts, and attractions like Black Point Estate and Gardens where your group can tour the historic grounds.

a group of young people playing music on the beach

Lake Geneva Public Beach (Riviera Beach)

Highlights: family-friendly seasonal activities, swimming lessons

Address: Lake Geneva, WI 53147
Phone: (262) 248-3673

Big Foot Beach State Park

Highlights: swimming, canoeing, kayaking, and hiking

Address: 1550 S Lake Shore Dr, Lake Geneva, WI 53147
Phone: (262) 248-2528

Fontana Beach

Highlights: beachfront grassy areas and playground

Address: Fontana Blvd, Fontana-On-Geneva Lake, WI 53125

Phone: (262) 275-6136

Charter bus travel tip: Lake Geneva is a heavily residential area, and you’ll find that many beaches offer resident discounts for beach admission and parking options. If you’re traveling with a big group, call ahead to verify oversized parking availability and group admission rates for out-of-towners.

4.   Oglesby, IL

Distance from Chicago: 1.5 hours or ~100 miles

Groups of nature enthusiasts should make a trip from Chicago to Oglesby for beautiful walking and hiking opportunities. This quaint town is home to some of the state’s most breathtaking parks, all situated along the Illinois and Vermillion rivers. Starved Rock State Park and Matthiessen State Park have miles of hiking trails, water features, rock formations, nature-watching activities, and picnic areas. Matthiessen State Park has several activities your group can enjoy but doesn’t have accommodations like Starved Rock.

Consider starting your day of hiking at Matthiessen and then moving along to Starved Rock for more hiking and a bite to eat at the Starved Rock Lodge Restaurant or Back Door Lounge. Starved Rock also has rustic, spacious venues that are often used for business conferences and wedding services. With a charter bus rental, you can easily shuttle your wedding or business guests from Chicago to the great outdoors for a secluded event.

A waterfall at Starved Rock State Park.

Starved Rock State Park

Highlights: St. Peter’s sandstone rock formations, river cruises, guided trolley tours

Address: 2668 E 875th Rd, Oglesby, IL 61348
Phone: (815) 667-4726

Matthiessen State Park

Highlights: Cascade Falls, canyons, horseback riding trails

Address: 2500 IL-178, Oglesby, IL 61348
Phone:  (815) 667-4868

Charter bus travel tip: Parking can quickly fill up later in the afternoon at both parks, and you may not have an option for your charter bus. You can organize a drop-off and pick-up time with your driver and reserve parking in town. Oglesby has a few hotels, public lots, and campgrounds that allow parking for oversized vehicles.

5.   Madison, WI

Distance from Chicago: 2.5 hours or ~150 miles

As the capital of Wisconsin and a major college city, Madison has a little bit of something for everyone. From educational, historic attractions to rowdy yet fun nightlife, your group will find plenty to do. The Wisconsin State Capitol is a spectacular location to learn about history and admire grand Beaux-Arts architecture. Free tours are available every day, and groups of 10 or more can request a private tour with a prior reservation.

The Olbrich Botanical Gardens are another popular educational spot. Located about 5 miles north of the capitol, they are a lovely place to learn about exotic tropical plants, native flora and fauna, and international cultures.

The area around University of Wisconsin-Madison has a variety of nightlife options for college-aged adults wanting to enjoy an evening out on the town. Traveling with kids or even prospective students? Try to catch a thrilling Badgers football game at Camp Randall Stadium during the season, or tour the beautiful campus off of Lake Mendota.

the Thai Pavilion at Olbrich Botanical Gardens

Wisconsin State Capitol

Highlights: observation deck with views of the city, hand painted murals, seasonal events

Address: 2 E Main St, Madison, WI 53703

Phone: (608) 266-0382

Olbrich Botanical Gardens

Highlights: Thai pavilion (the only structure of its kind in the contiguous U.S.), Boltz Indoor Conservatory, butterfly exhibits

Address: 3330 Atwood Ave, Madison, WI 53704

Phone: (608) 246-4550

University of Wisconsin-Madison

Highlights: waterfront views from Memorial Union Terrace, local businesses along State Street

Address: 716 Langdon St, Madison, WI 53706

Phone: (608) 263-2400

Charter bus travel tip: Motorcoach parking in Madison is available at Turville Point Park, just a couple miles from downtown. Have your driver safely drop your group off at your destination of choice before they park at Turville.

Book Your Chicago Day Trip Today

Get your day-trip planning started with GOGO Charters! A GOGO Charters rental expert will assist you at 312-546-3925 when you’re ready to book a minibus or charter bus for your trip. Is your group organizing a longer outing? GOGO Charters has your multi-day trip transportation covered from Chicago to Indianapolis, Detroit, St. Louis, and beyond.