The Gap Travel Guide
Chicago
Popular places to visit
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
McCormick Place
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Six Flags Great America
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Things to do
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Architecture Center River Cruise aboard First Lady
Top hotels in The Gap
Embassy Suites by Hilton Chicago Downtown River North
First I made phone call day earlier before arriving Ruth answered the phone and her customer skills was absolutely amazing from there on it was great experience . To have to pay for early check in gets me upset because if check out early hotel does not reimburse me back
Reviewed on 11 Nov 2025
Hilton Chicago/Magnificent Mile Suites
Everything. Loved the experience.
Reviewed on 12 Nov 2025
Congress Plaza Hotel
a
Reviewed on 8 Nov 2025
citizenM Chicago Downtown
The rooms are smaller than usual, but super clean and convenient. They're nice for a night or 2. A couple issues...there is no plug near the bed, so if you have something like a CPAP machine, bring an extension cord. Also, the bathroom has no fan. Be prepared to leave if you're partner has to relieve ...
Reviewed on 8 Nov 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Rooms are clean, we were first assigned in a room next to the elevator. It was noisy at night so we requested to be transfered to a different room. We were transfered right away.
Reviewed on 9 Nov 2025
Freehand Chicago
The gent at the front desk was very friendly. The room and hotel were clean. Was the room small? Yes. Buy I don't need a ton of space. I'd stay here again.
Reviewed on 11 Nov 2025
Other neighbourhoods around The Gap
Near South Side
Travellers choose Near South Side for its ample dining options. Hop aboard the metro at Cermak-McCormick Place Station or Roosevelt Station and check out top sights like Soldier Field.
South Loop
Soldier Field and Lake Michigan are a few top attractions in South Loop. Hop around the city on the metro at Roosevelt Station or Cermak-McCormick Place Station and check out the area's fascinating museums, panoramic lake views and popular shops.
Hyde Park
Hyde Park is noteworthy for its museums, and you can make a stop at top attractions like Lake Michigan and Robie House.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).
The Loop
Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.
West Loop
Consider a visit to Milwaukee Avenue and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.
