7 things to do in Chicago in under two hours


If you’re headed to Chicago for business and happen to have some free time between work and meetings, the Windy City isn’t short on things to do in a limited amount of time. Have a look for yourself at our seven things to do in Chicago in under two hours.

Spending the day eating hotdogs at Wrigley Field, or being mesmerized for hours at the world-famous Shedd Aquarium are both great options for how to spend time in Chicago. Unfortunately, not all of us have all the extra free time in the world. Especially during business trips, it’s hard to find the time to see a city the way we wish we could. See if one of the suggestions below sounds like something you would want to make time for. 

Chicago Riverwalk

Take the steps down from North Michigan Avenue to the new Chicago Riverwalk, which runs along the south bank from Lake Michigan to Lake Street. The McCormick Bridgehouse and Chicago River Museum offer a glimpse of the city’s river history, if there’s time to stop by either. Otherwise, the Centennial Fountain shoots its arc of water across the river on the hour and that’s worth timing out. Six cafes line the walk, offering eye-level peeks at busy river traffic.

For history buffs and also for a more sober moment, Chicago has a Vietnam Veterans Memorial on the Riverwalk. Here, you will find a black granite slab bearing the names of those killed.

Museum of Contemporary Art

For a quick tour of highlights, hop on one of the free 45-minute tours, located just one block east of the Magnificent Mile. The docent-led tours often focus on the current exhibition as well as pieces from the standing collection. The tours vary depending on days, times and docents. There is an admission price to enter the museum which houses a permanent collection of more than 2,500 objects of visual art from 1945 to the present. The museum is closed on Mondays and has free admission on Tuesdays, plus free jazz concerts on Tuesday evenings through early fall.

Navy Pier

Chicago’s Navy Pier has been a landmark destination for locals and tourists alike. It recently celebrated its 100th anniversary in 2016 and has continuously been reinventing itself year after year, adding more and more attractions and things to do, so that visitors can always find something new each time they visit. Navy Pier has restaurants, rides & games, cultural attractions, live entertainment and public art and exhibitions.

Promontory Point

Jutting into Lake Michigan, Promontory Point is a 12-acre oasis where visitors can spend some time in peace and quiet. Located within Hyde Park, a path winds around the 1930s photogenic field house, which was built of Wisconsin Lannon stone. The neighborhood is also home to the University of Chicago and the Obama family. The park is free to visitors and once inside, you can spend time exploring the 70-year old grounds. Take in views of sailboats, the city skyline, waves crashing against the seawall and fitness fanatics cycling or running on the lakefront path. The easiest way to get there is to take the 55th Street underpass 6 miles south of the Loop and head east of Lake Shore Drive. Parking is free.

Robie House

If you’re into architecture, then the name Frank Lloyd Wright should be familiar. In Chicago, you can spend a couple hours exploring Frank Lloyd Wright’s architecture at the Robie House. It is known as a mecca for Frank Lloyd Wright enthusiasts, conveniently located without having to leave the city limits. The Robie House in Hyde Park exemplifies Wright’s signature Prairie School style, both in its external appearance and interior design. You can take a peek inside the historic home (and get some decorating ideas) by taking a tour led by the Frank Lloyd Wright Trust, offered five days a week.

Hot “G” Dog

You can’t come to Chicago and not eat a real Chicago hot dog! (Unless you’re a vegetarian/vegan, and if that’s the case, you might want to skip to our next suggestion.) There was once a time when Chicagoans would line up to eat at Hot Doug’s. It shut down years ago, but the owner, Doug Sohn, left a worthy heir to his encased meat throne. Located in Uptown, Hot “G” Dog is run by a group of cooks who formerly prepared the orders at Hot Doug’s. Serving a menu similar to the one offered at the old Avondale stand, you’ll find great Chicago dogs. Look forward to sausages made with alligator or goat meat and duck fat fries on the weekends—arrive with an appetite.

Lakefront Trail

Sometimes what we need during our downtime is to do some fitness. Working out can help relieve stress and clear your mind, especially when you are working out alongside a gorgeous lake. The Lakefront Trail runs from the North Side of Chicago to 71st Street on the South Side. The Lakefront Trail provides an 18-mile path along the coast of Lake Michigan that connects neighborhoods throughout the city. Once you’re on the path, you’ll typically find bicyclists zooming by, joggers pounding the pavement and pedestrians out for a leisurely stroll. No matter which way you decide to enjoy the Lakefront Trail, make sure to make time to enjoy the epic Chicago skyline.

Cut down on the amount of time you spend traveling around the sights by booking Blacklane’s chauffeur service in Chicago. Let us know what your top tips are for the Windy City on our social channels!