Woodlawn Travel Guide
Chicago
Popular places to visit
Jackson Park
Jackson Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its fascinating museums.
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.
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.
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.
Things to do
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Top hotels in Woodlawn
Hotel Felix River North/Magnificent Mile
Hidden daily “urban” fee. Cost me as much as a whole night’s worth stay. Would have chosen a different hotel had the hidden extra daily fee been made clear when booking, rather than finding out when I’m checking in and it’s too late. A real drag on my vacation trip.
Reviewed on 27 Apr 2026
River Hotel
Everything was great until morning then our room filled up with smoke otherwise it was good
Reviewed on 27 Apr 2026
Club Quarters Hotel, Central Loop, Chicago
Quite. Clean, Safe
Reviewed on 27 Apr 2026
Hotel Riu Plaza Chicago
Everything
Reviewed on 28 Apr 2026
Hilton Chicago/Magnificent Mile Suites
We had issues with the heater so we just asked for extra blankets as the room remained cold
Reviewed on 28 Apr 2026
Holiday Inn Chicago Dwtn - The Mart by IHG
The pool was ice cold.
Reviewed on 27 Apr 2026
Other neighbourhoods around Woodlawn
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 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.
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.
