Woodlawn Hotels, Chicago

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Our top choices for Woodlawn hotels

Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.0 star property
Woodlawn
3.8 out of 10, (58 reviews)
"Parking"
United States
Sydney
The price is AU$123
includes taxes & fees
24 Apr - 25 Apr
Best Motel By OYO Chicago I-90

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 12.6 km from Woodlawn
9.4 out of 10, Exceptional, (2,418 reviews)
"Great spot and view, would stay again!"
United States
Kimberly
The price is AU$315
includes taxes & fees
6 Apr - 7 Apr
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (2,703 reviews)
"Amazing place to stay!"
United States
Nia
The price is AU$261
includes taxes & fees
5 Apr - 6 Apr
Hilton Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,221 reviews)
"Excellent stay."
United States
Fenton
The price is AU$334
includes taxes & fees
8 Apr - 9 Apr
Swissotel - Chicago

The Wade

The Wade
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.4 out of 10, Very good, (1,751 reviews)
"Staff was friendly, explained the hotel and amenities well. Great location."
United States
Mary
The price is AU$283
includes taxes & fees
26 Mar - 27 Mar
The Wade

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.1 km from Woodlawn
9.4 out of 10, Exceptional, (2,038 reviews)
"Great location and very clean hotel with nice staff. "
United States
Carrie
The price is AU$267
includes taxes & fees
26 Mar - 27 Mar
Arlo Chicago

River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,024 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is AU$162
includes taxes & fees
13 Apr - 14 Apr
River Hotel

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Theatre District, 12.2 km from Woodlawn
9.2 out of 10, Wonderful, (1,409 reviews)
"Check in was quick and easy, room was clean and spacious "
United States
Quinton
The price is AU$310
includes taxes & fees
31 Mar - 1 Apr
Sports Illustrated Resorts Chicago

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (10,017 reviews)
"Clean room, nice hotel, nice staff"
United States
Melanie
The price is AU$195
includes taxes & fees
1 Apr - 2 Apr
Congress Plaza Hotel

Pendry Chicago

Pendry Chicago
4.5 star property
Theatre District, 12.2 km from Woodlawn
9.2 out of 10, Wonderful, (1,123 reviews)
"Staff really friendly and hotel was clean and close to everything around the city can’t wait to come back. "
United States
Pablo Ibarra
The price is AU$377
includes taxes & fees
12 Apr - 13 Apr
Pendry Chicago

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, (1,322 reviews)
"Very beautiful place to stay"
United States
angie
The price is AU$213
includes taxes & fees
29 Mar - 30 Mar
The Chicago Hotel Collection Ambassador Gold Coast

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, (3,411 reviews)
"Wonderful hotel, friendly and accommodating staff! "
United States
Chevon
The price is AU$178
includes taxes & fees
26 Mar - 27 Mar
Club Quarters Hotel, Central Loop, Chicago

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, (2,338 reviews)
"Beautiful property, great resturant on site, an the pool and spa was amazing."
United States
Tim
The price is AU$261
includes taxes & fees
5 Apr - 6 Apr
Palmer House a Hilton Hotel

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (3,628 reviews)
"Good hotel , clean , staff great, Good location"
United Kingdom
Martin
The price is AU$273
includes taxes & fees
6 Apr - 7 Apr
Hotel Riu Plaza Chicago

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 12.4 km from Woodlawn
9.4 out of 10, Exceptional, (3,618 reviews)
"Great room great place to stay "
United States
Adrian Mark
The price is AU$401
includes taxes & fees
26 Mar - 27 Mar
LondonHouse Chicago, Curio Collection by Hilton

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
The Loop, 12.4 km from Woodlawn
9.4 out of 10, Exceptional, (3,339 reviews)
"I loved my stay"
United States
Janet
The price is AU$312
includes taxes & fees
5 Apr - 6 Apr
The Royal Sonesta Chicago Downtown

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (2,133 reviews)
"Great stay!"
United States
Hannah
The price is AU$194
includes taxes & fees
7 Apr - 8 Apr
Club Quarters Hotel Wacker at Michigan, Chicago

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13.1 km from Woodlawn
9.0 out of 10, Wonderful, (3,326 reviews)
"Great stay "
United States
Mariah
The price is AU$204
includes taxes & fees
30 Mar - 31 Mar
Eurostars Magnificent Mile

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
River North, 13.1 km from Woodlawn
8.6 out of 10, Excellent, (512 reviews)
"Lots of stuff close by , cool vibe inside and very nice staff"
United States
Abel
The price is AU$140
includes taxes & fees
7 Apr - 8 Apr
FOUND Hotel Chicago River North

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, (2,236 reviews)
"Great stay!"
United States
Jessica
The price is AU$327
includes taxes & fees
4 Apr - 5 Apr
Silversmith Hotel Chicago Downtown
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.

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.

Magnificent Mile

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

The Loop

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

O'Hare

Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago.

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.

Top Woodlawn Hotel Reviews

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 50 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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