Woodlawn Travel Guide
Tourist Guide
Visit Woodlawn
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
Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.
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 waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
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.
Activities
Chicago Sightseeing River and Lake Cruise
Wendella's 90-min Chicago River Architecture Tour
Chicago Crime and Mob Bus Tour
Our pick of the best Woodlawn Hotel Deals
Congress Plaza Hotel
"Our room was spacious and clean. Everything works and soundproofing was great in a busy hotel. The only could make it better would be adding a door to the main bedroom and slightly larger TV (or just completely get rid of it)."
Reviewed on 25 June 2026
Hilton Chicago/Magnificent Mile Suites
"Good location, bar and brunch were great. View from the pool and fitness centers was u real. Room was clean but sink faucet was loose and leaking and the bathroom door locks didn’t work well or would stick. Other than that it was nice."
Reviewed on 24 June 2026
The Chicago Hotel Collection - Magnificent Mile
"This Hotel is in the TOP 5 on my list for Chicago as it’s easy to get to where your going without driving, everything is taken care for you from the minute you walk through the revolving doors, A BIG YES TO STAYING AGAIN THE FUTURE"
Reviewed on 25 June 2026
Hyatt Regency O'Hare Chicago
"Right next to the convention center and Rosemont Theatre which made it very easy to walk around. Breakfast was not included, but there were a lot of restaurant options available. Staff was extremely friendly and professional."
Reviewed on 25 June 2026
The Chicago Hotel Collection Ambassador Gold Coast
"The Ambassador Gold Coast was our first hotel stay as we embarked on an AmTrak Rail Pass trek across the country and back, and they set the bar very high! The staff was very helpful, the room was large with a big window, very clean, great bed, and nice bathroom. The buffet breakfast (included) was ..."
Reviewed on 24 June 2026
River Hotel
"El hotel 10 de 10 está en una buena área y el servicio excelente limpian tu cuarto todos los días que estés no tienes desayuno incluido pero an lado está un restaurante para desayunar comer y cenar 😊"
Reviewed on 24 June 2026
Our guide on where to stay in Woodlawn
Downtown Chicago
Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
Magnificent Mile
Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.
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.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Oz Park, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.
