A wooden bridge over a calm river, surrounded by lush greenery and a distant building.

Woodlawn Hotels, Chicago

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Check prices for these dates

This weekend
26 June - 28 June
Next weekend
3 July - 5 July

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Our top choices for Woodlawn hotels

Lobby

Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.5 star property
Woodlawn
3.6 out of 10, (92 reviews)
"This is not a good place."
United States
Dinesh Kumar
The price is AU$169
includes taxes & fees
13 July - 14 July
Best Motel By OYO Chicago I-90
Lobby

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 14.4 km from Woodlawn
8.2 out of 10, Very good, (1,644 reviews)
"Very good location, breakfast is fantastic, dinner and bar are great."
United States
Zhiwen
The price is AU$198
includes taxes & fees
5 July - 6 July
The Chicago Hotel Collection Ambassador Gold Coast
Lobby

River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,260 reviews)
"Excellent place to stay, as we found it central & walkable to most parks & attractions. The place was spotless & the staff were fantastic."
Canada
Jody
The price is AU$268
includes taxes & fees
5 July - 6 July
River Hotel
Cocktail bar

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 12.9 km from Woodlawn
7.8 out of 10, Good, (3,134 reviews)
"It was good place to stay for the Go Fest Event"
United States
Ken
The price is AU$265
includes taxes & fees
5 July - 6 July
Freehand Chicago
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (10,129 reviews)
"Great stay!"
United States
Daniel
The price is AU$235
includes taxes & fees
29 June - 30 June
Congress Plaza Hotel
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 11.9 km from Woodlawn
9.4 out of 10, Exceptional, (1,116 reviews)
"Good location, friendly staff"
United Kingdom
Philip
The price is AU$316
includes taxes & fees
6 July - 7 July
Staypineapple, An Iconic Hotel, The Loop
Exterior detail

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
River North, 13.1 km from Woodlawn
8.4 out of 10, Very good, (649 reviews)
"Excellent stay in good location"
United States
Nicholas
The price is AU$210
includes taxes & fees
28 June - 29 June
FOUND Hotel Chicago River North
Reception

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 11.7 km from Woodlawn
8.6 out of 10, Excellent, (2,496 reviews)
"Beautiful place to stay."
United States
Charles Otto
The price is AU$429
includes taxes & fees
1 July - 2 July
Palmer House a Hilton Hotel
2 bars/lounges

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3,437 reviews)
"Staff was great."
United States
Marianne
The price is AU$394
includes taxes & fees
5 July - 6 July
Hyatt Regency Chicago
Nightclub

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.6 km from Woodlawn
8.6 out of 10, Excellent, (2,193 reviews)
"Great hotel with awesome location"
United States
Daniel
The price is AU$227
includes taxes & fees
1 July - 2 July
Central Loop Hotel
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13.1 km from Woodlawn
9.0 out of 10, Wonderful, (3,677 reviews)
"Had an amazing stay here!"
United States
Audrey
The price is AU$275
includes taxes & fees
2 July - 3 July
Eurostars Magnificent Mile
Presidential Suite, 1 Bedroom, Non Smoking

Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown
4.0 star property
River North, 13 km from Woodlawn
8.8 out of 10, Excellent, (1,566 reviews)
"Great stay"
United States
Matt
The price is AU$274
includes taxes & fees
1 July - 2 July
Hotel 55 Chicago Downtown
Lobby

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 11.7 km from Woodlawn
9.2 out of 10, Wonderful, (2,260 reviews)
"Wonderful stay"
United States
Taylor
The price is AU$252
includes taxes & fees
5 July - 6 July
Silversmith Hotel Chicago Downtown
2 restaurants; breakfast, lunch, dinner and brunch served

The Hoxton, Chicago

The Hoxton, Chicago
4.0 star property
12.7 km from Woodlawn
9.2 out of 10, Wonderful, (1,000 reviews)
"Great hotel!!"
United States
Stacey
The price is AU$454
includes taxes & fees
1 July - 2 July
The Hoxton, Chicago
Serves breakfast, lunch and dinner

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
River North, 13 km from Woodlawn
9.4 out of 10, Exceptional, (999 reviews)
"Great place!"
United States
Kelly
The price is AU$248
includes taxes & fees
1 July - 2 July
Moxy Chicago Downtown
Exterior

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.1 km from Woodlawn
9.4 out of 10, Exceptional, (2,131 reviews)
"Excellent hotel! Will definitely stay again."
United States
Justin
The price is AU$318
includes taxes & fees
1 July - 2 July
Arlo Chicago
Champagne service

The Buckingham Hotel

The Buckingham Hotel
3.5 star property
The Loop, 11.3 km from Woodlawn
9.0 out of 10, Wonderful, (1,001 reviews)
"The view of the city was spectacular"
United States
Wilmer
The price is AU$240
includes taxes & fees
1 July - 2 July
The Buckingham Hotel
2 bars/lounges, rooftop bar

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel
4.5 star property
Theatre District, 12.2 km from Woodlawn
9.0 out of 10, Wonderful, (1,016 reviews)
"Great hotel to stay."
United States
Josias
The price is AU$384
includes taxes & fees
5 July - 6 July
theWit Chicago, a Hilton Hotel
Lobby

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 10.9 km from Woodlawn
7.6 out of 10, Good, (2,634 reviews)
"Great location and helpful staff."
United States
Ming
The price is AU$243
includes taxes & fees
8 July - 9 July
Travelodge by Wyndham Downtown Chicago
Nightclub

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 11.6 km from Woodlawn
8.8 out of 10, Excellent, (3,551 reviews)
"The on-site restaurant was excellent"
United States
William
The price is AU$236
includes taxes & fees
28 June - 29 June
Club Quarters Hotel, Central Loop, Chicago
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.
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Our guide on where to stay in Woodlawn

Find the best Woodlawn areas for the activities you enjoy most.

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

A historic castle-like building with intricate stonework and a paved walkway.

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

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

The Loop

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Top Woodlawn Hotel Reviews

Recent Reviews in Woodlawn

Freehand Chicago

Freehand Chicago

10/10 Excellent
"Our stay was great, we had a minor maintenance issue and hotel staff was on it and fixed it immediately. Overall great value for the money."
Clint 3-night trip
Posted less than an hour ago
Freehand Chicago

Frequently asked questions

What's it like in Woodlawn?
Woodlawn is a neighbourhood that travellers like for its beaches, restaurants and gardens. Looking for sights you might find in a travel guide about Woodlawn? Consider a visit to Lake Michigan while you're in the neighbourhood.
Where is the best place to stay in Woodlawn?
Based on Expedia customer reviews, Best Motel By OYO Chicago I-90 is the highest ranked property in Woodlawn. This property offers free valet parking and flat-screen TVs.
How many hotels are there in the Woodlawn area?
If you're searching for places to stay in Chicago, Expedia has something to meet your needs with 46 Woodlawn hotels and other accommodation options to choose from.
If I need to cancel my hotel reservation in Woodlawn, will I receive a refund?
Yes, the majority of hotel room reservations are refundable provided that you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you have a non-refundable reservation, you might still have the option to cancel and be given a refund within a 24-hour period of booking. Enter dates in and click on "Search", then filter by "fully refundable" to view the best deals available in Woodlawn.
What can I see and do in this Chicago neighbourhood?
Spend some time exploring the great outdoors at Lake Michigan, Jackson Park and Bob-O-Link Meadow. 63rd Street Beach and Lorado Taft's Midway Studios are also a couple of places to visit in the neighbourhood. Oak Woods Cemetery, Stony Island Arts Bank and Rockefeller Memorial Chapel are just a few of the places to visit in and around Woodlawn. While you're out sightseeing in Chicago, make sure that you visit other sights such as Oriental Institute Museum or Bond Chapel.
How can I get around Woodlawn and the greater Chicago area?
Looking for a quick way to explore more of the city? Catch a ride on metro transit at Cottage Grove Station and King Drive Station. To venture out of town, take a train from Chicago 63rd Street Station.

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