Woodlawn

Chicago

A wooden bridge over a calm river, surrounded by lush greenery and a distant building.
A clear blue sea with visible rocks and a partly cloudy sky.

Stay near popular Woodlawn attractions

Jackson Park

7.4/10 (9 reviews)
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.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

P1,685
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

P2,496
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

P2,647
per adult
90% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

P2,527
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

P9,905
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Spirit of Chicago Signature Lunch Cruise on Lake Michigan

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

P5,393
per adult
City Cruises Chicago: Signature Lunch Cruise on Lake Michigan
See all activities in Chicago

Top hotels in Woodlawn

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is P8,473 per night from Nov 2 to Nov 3
P8,473
P10,074 total
Nov 2 - Nov 3
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,141 reviews)
"The first"

Reviewed on Oct 9, 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is P9,569 per night from Oct 25 to Oct 26
P9,569
P11,377 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
The price is P8,992 per night from Nov 1 to Nov 2
P8,992
P10,690 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (2,450 reviews)
"Beautiful hotel in a great location. Complimentary coffee, beautiful dining room, bar and lounging spots. Will definitely return!"

Reviewed on Oct 9, 2026

The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is P8,602 per night from Nov 1 to Nov 2
P8,602
P10,227 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
The Chicago Hotel Collection - Magnificent Mile
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
The price is P8,931 per night from Nov 1 to Nov 2
P8,931
P10,618 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
The Wade
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is P10,424 per night from Oct 30 to Oct 31
P10,424
P14,239 total
Oct 30 - Oct 31
includes taxes & fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (3,399 reviews)
"Clean room and convenient to city walk."

Reviewed on Oct 9, 2026

Hilton Chicago
See all 4,439 properties in Woodlawn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Where to stay in Woodlawn

Find the best Woodlawn areas and neighborhoods for the activities you enjoy most.
A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

Magnificent Mile

Michigan Avenue and Chicago Water Tower are just a few worthwhile attractions to visit in Magnificent Mile. Travelers also love the fascinating museums, panoramic lake views, and popular shops.

A river with yellow boats, a bridge, and tall buildings.

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.

A large, historic building with a central tower and multiple windows, located near a body of water.

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.

A river with a city skyline in the background, surrounded by green trees and grass.

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 Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

Woodlawn