What to See and Do as a Group in Chicago

Ready to start planning that reunion trip for your college friends who are spread across the country? Or perhaps you’ve been tasked with organizing a family reunion with members sprawled from coast to coast? Home to the Magnificent Mile and Wrigley Field, Chicago is not only where deep-dish pizza was invented, but also a prime location for travelers of all ages to meet in the middle of the country for vacation. Located on the shores of Lake Michigan, the Windy City offers travelers its charm and hundreds of attractions to explore.

Getting There

• Drive 11 miles northeast from Midway Airport
• Drive 18 miles southeast from Chicago O’Hare International Airport

If you’re planning to explore the city a bit with your group before picking up your car, you can easily rent from Alamo’s 203 N. LaSalle St. location, which is downtown near the Chicago Transit Authority Clark/Lake station and is accessible by the Blue or Orange train lines.

Lake Shore Drive: Your Access to Everything

Chicago’s Lakeshore Drive overlooks Lake Michigan. Along this scenic north-south expressway, visitors can access the Museum of Science and Industry, Navy Pier, Shedd Aquarium, Soldier Field and more. Park at the Diversey Driving Range in Lincoln Park, where you’ll pay only $18 for the day.

What to See and Do

Navy Pier: A Century of Chicago History

Sporting the iconic Centennial Wheel, a planetarium, an IMAX theater and a variety of other family-friendly activities, Navy Pier is a staple along Chicago’s lakefront.

The Ferris wheel is a tribute to Chicago — and amusement park history — with roots dating back to the 1893 World’s Fair. Passengers can get incredible views of the city from atop the 200-foot Centennial Wheel, which opened during summer 2016 to commemorate Navy Pier’s 100th birthday. (Its predecessor wheel closed in 2015 after a 10-year run.) Each Ferris wheel gondola holds up to eight people, which is great for groups looking to ride together. Tickets for a ride run $15 for adults and $12 for children ages 3-11.

Legendary Bites: Burgers, Pizza and Italian Beef Sandwiches

Afterward, grab a meal on the pier at the Billy Goat Tavern or Harry Caray’s Tavern, which both offer unique Chicago dining. The Billy Goat’s kaiser roll burgers are legendary, while the homemade potato chips at Harry Caray’s make for a savory complement to an ice-cold lager.

Reserve an hour or two to experience a deep-dish pizza from Giordano’s. It can easily feed a family of four, but be prepared to get comfortable because the Midwestern staple takes time to bake. Got a bigger group? Order more pies with a variety of toppings to accommodate each member of your group’s tastes. If you’re tight on time, try another regional specialty, such as Italian beef sandwiches or pasta.

John G. Shedd Aquarium: An Ocean by the Lake

From Navy Pier, jump onto a water taxi — one of the most fun and affordable ways to get larger travel groups between the pier and downtown. Upon exiting your water taxi, walk right up to Shedd Aquarium, home to more than 1,500 species of fish, a touch tank of live stingrays and a myriad of exhibits like Amazon Rising and At Home on the Great Lakes. Visitors can also explore the Abbott Oceanarium, the first to bring white-sided dolphins and sea otters to Chicago. Shedd’s staff advises buying tickets online in advance, especially during summer and major holidays.

Millennium Park: Bean Time in Chicago

Make your way back into the heart of the city, where one of Chicago’s popular meeting places awaits at Cloud Gate in Millennium Park. If you’re coming from the museums, hop on Lake Shore Drive South for just under 2 miles to reach the park.

A group photo in front of Cloud Gate, colloquially known as The Bean, is a staple of any trip to the Windy City. Or take your photo in The Bean’s reflection. The Bean is flanked by outdoor activities for kids and families and, on any given weekend during the summer, live music, festivals and entertainment.

If a free concert doesn’t engage the little ones, nearby Maggie Daley Plaza could be the answer to entertain your adventure-seekers. The plaza features an outdoor rock climbing center (open April through October) and an ice skating track in winter. The play garden — 3 acres filled with unique sculptures and structures that inspire and encourage play — is open until 9 p.m. daily.

Magnificent Mile: World-Famous Brands

Shoppers in your group can freshen up their wardrobes along this mile of shops, restaurants and designer boutiques extending along Michigan Avenue from the DuSable Bridge to the Drake Hotel at Lake Shore Drive.

A highlight of the Mag Mile, as it’s affectionately referred to by locals, is the 100-story John Hancock Center. Ride the elevator up to the 96th floor’s Signature Room Lounge. Here you’ll get a 360-degree look at the city for the cost of a drink or an appetizer, or make a reservation for your group to enjoy a full dinner at the Signature Room, located one floor beneath the lounge. Note that parties of six to 11 require a credit card on file to hold the reservation. Looking north from either room, you can see the silhouette of the Chicago Cubs’ home, Wrigley Field, while a southward glance features the immensity of Willis Tower and the industrial skyline.

Where to Stay

At the centrally-located Wyndham Grand Chicago Riverfront, visitors have easy access to Michigan Avenue and Millennium Park. The hotel offers free internet and pet-friendly room options for those traveling with furry companions. Be sure to ask about the hotel’s special ticket rates for Broadway musicals and other city activities. Additionally, guests can take advantage of the hotel’s Drive-In Package, which offers a 30-percent discount for overnight valet parking. The Wyndham features oversized rooms and a variety of suite options that are well suited to accommodate group travel.

In the theater and financial district, your group can lodge in the historic Palmer House Hilton. More than 140 years old, the Palmer House is within walking distance to the Magnificent Mile and centrally located for you and your group to use as a meeting point after daily activities. Some Hip and Historic guest rooms feature two beds and two bathrooms, making them an ideal option for families or groups.