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.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
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.
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.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Things to do
360 CHICAGO Observation Deck
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Wendella's 90-min Chicago River Architecture Tour
Top hotels in The Gap
Congress Plaza Hotel
Bed was super comfy and location was great.
Reviewed on 9 Apr 2026
Hilton Chicago/Magnificent Mile Suites
Valet takes forever even if u call ahead
Reviewed on 9 Apr 2026
Embassy Suites by Hilton Chicago Downtown River North
The rooms were great and we enjoyed the view of Chicago. The mezzanine and hallways were noisy on Easter night (and especially on the night before Easter) but the kids were sleeping on the fold-out couch and they didn’t mind, but the bedroom was quiet because it faced the outside. We loved the breakfast ...
Reviewed on 8 Apr 2026
Hotel Riu Plaza Chicago
I have travelled for most of my business career. As a result, I have had the opportunity to stay in numerous hotels across the US and internationally. Here are the pluses for The Riu Plaza Chicago: 1) Brand new. Spotlessly clean-very comfortable beds and new linens. Pillows soft and firm, just right ...
Reviewed on 8 Apr 2026
Hilton Chicago O'Hare Airport
We ate at the restaurant and the food was excellent. Very happy with our stay.
Reviewed on 7 Apr 2026
The Wade
Clean room and well staffed, would 100% coma back
Reviewed on 7 Apr 2026
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.
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 Polk Station (Pink Line) or Racine Station to get around town.
