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.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
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.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Things to do
Chicago Sightseeing River and Lake Cruise
Chicago By Night River & Lake Cruise
Odyssey Lake Michigan Premier Dinner Cruise
Wendella's Lake and River Architecture Tour
Top hotels in The Gap
Congress Plaza Hotel
Reviewed on 25 Sept 2025
Freehand Chicago
Reviewed on 24 Sept 2025
Embassy Suites by Hilton Chicago Downtown River North
Reviewed on 25 Sept 2025
Hilton Chicago/Magnificent Mile Suites
Reviewed on 25 Sept 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Reviewed on 24 Sept 2025
InterContinental Chicago Magnificent Mile by IHG
Reviewed on 27 Sept 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.
Near West Side
Live music, theatres and shopping highlight some notable features of Near West Side. Make a stop by United Center or Credit Union 1 Arena while you're visiting, and jump aboard the metro at Racine Station or Polk Station (Pink Line) to get around town.
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.
The Gap Travel Guide
- Wrigley Field
- Navy Pier
- Millennium Park
- Grant Park
- Chicago Riverwalk
- Lake Michigan
- Northwestern University
- Art Institute of Chicago
- Willis Tower
- Chicago Theatre
- Allstate Arena
- Chicago Museum of Science and Industry
- Field Museum of Natural History
- Water Tower Place
- University of Illinois Chicago
- Northwestern Memorial Hospital
