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Hotels in Woodlawn, 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
3.4 out of 10, (48)
"Clean room "
United States
Pierre
The price is RM227
RM295 total
includes taxes & fees
13 Jan - 14 Jan 2026
Best Motel By OYO Chicago I-90

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 12.9 km from Woodlawn
8.0 out of 10, Very good, (2658)
"It's an excellent place."
United States
Jose
The price is RM238
RM350 total
includes taxes & fees
4 Jan - 5 Jan 2026
Freehand Chicago

River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (4856)
"Great location, comfortable room, and nice staff."
United States
Claudia
The price is RM331
RM389 total
includes taxes & fees
6 Jan - 7 Jan 2026
River Hotel

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (9698)
"Wonderful stay!"
United States
Zach
The price is RM315
RM369 total
includes taxes & fees
26 Dec - 27 Dec
Congress Plaza Hotel

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (2966)
"Great place to stay"
United States
Elisha
The price is RM374
RM438 total
includes taxes & fees
30 Dec - 31 Dec
Aloft Chicago Mag Mile

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3417)
"The Hotel was amazing great location "
United States
Donnisha
The price is RM589
RM810 total
includes taxes & fees
10 Jan - 11 Jan 2026
Hyatt Regency Chicago

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, (2285)
"Great staff and restaurants!!"
United States
Abigale
The price is RM380
RM584 total
includes taxes & fees
15 Jan - 16 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 12.7 km from Woodlawn
8.2 out of 10, Very good, (2762)
"Excellent place to stay "
United States
Teniesha
The price is RM343
RM522 total
includes taxes & fees
6 Jan - 7 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 12.8 km from Woodlawn
8.8 out of 10, Excellent, (2198)
"Great location, easy parking. "
United States
Maria
The price is RM346
RM406 total
includes taxes & fees
5 Jan - 6 Jan 2026
DoubleTree by Hilton Chicago - Magnificent Mile

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.1 km from Woodlawn
9.2 out of 10, Wonderful, (1902)
"Great hotel"
United States
Chris
The price is RM347
RM528 total
includes taxes & fees
8 Jan - 9 Jan 2026
Arlo Chicago

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, (3331)
"Great hotel "
United States
Anthony
The price is RM331
RM389 total
includes taxes & fees
6 Jan - 7 Jan 2026
Club Quarters Hotel, Central Loop, Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.4 out of 10, Very good, (2412)
"The room was clean and the staff was outstanding. "
United States
Albert
The price is RM496
RM701 total
includes taxes & fees
1 Jan - 2 Jan 2026
Hilton Chicago

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, (2015)
"Great stay"
United States
Kramer
The price is RM331
RM389 total
includes taxes & fees
6 Jan - 7 Jan 2026
Club Quarters Hotel Wacker at Michigan, Chicago

The Wade

The Wade
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.4 out of 10, Very good, (1533)
"Great staff and great location. "
United States
Joe
The price is RM378
RM443 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Wade

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 13.6 km from Woodlawn
8.2 out of 10, Very good, (3791)
"Clean room, good location, friendly staff"
United States
Zacharias
The price is RM311
RM365 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Whitehall Hotel, BW Premier Collection

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Magnificent Mile, 13.1 km from Woodlawn
8.4 out of 10, Very good, (3007)
"Enjoyed this hotel stay. "
United States
Kimberly
The price is RM325
RM500 total
includes taxes & fees
28 Dec - 29 Dec
Warwick Allerton - 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, (3458)
"Great hotel! "
United States
Kianna
The price is RM529
RM621 total
includes taxes & fees
4 Jan - 5 Jan 2026
LondonHouse Chicago, Curio Collection by Hilton

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 10.9 km from Woodlawn
7.4 out of 10, Good, (2496)
"Always a good stay"
Canada
Domenic
The price is RM304
RM357 total
includes taxes & fees
25 Jan - 26 Jan 2026
Travelodge by Wyndham Downtown Chicago

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (3042)
"Excellent stay great location and great rooms"
United States
Joseph
The price is RM405
RM589 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel Riu Plaza Chicago

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
River North, 12.8 km from Woodlawn
8.6 out of 10, Excellent, (4281)
"Friendly Staff, clean room, great area"
United States
LaTia
The price is RM316
RM371 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Garden Inn Chicago Downtown/Magnificent Mile
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 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

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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.

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).

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 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. Lorado Taft's Midway Studios and Jackson Park Driving Range 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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