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Top Trending Hotels Near Woodlawn, Chicago

Hallway
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 ₹5,040
₹6,546 total
includes taxes & fees
6 Jan - 7 Jan 2026
Best Motel By OYO Chicago I-90
Terrace/patio
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, (2178)
"Nice Hotel"
United States
Alan
The price is ₹8,044
₹9,442 total
includes taxes & fees
17 Dec - 18 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
River North, 13.1 km from Woodlawn
9.0 out of 10, Wonderful, (3140)
"Amazing and will be staying again!"
United States
Angie
The price is ₹8,423
₹9,888 total
includes taxes & fees
5 Jan - 6 Jan 2026
Eurostars Magnificent Mile
Reception
River Hotel

River Hotel

4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (4848)
"Location of the Hotel is very nice and the hotel is very clean."
United States
Khaing
The price is ₹7,484
₹8,785 total
includes taxes & fees
11 Dec - 12 Dec
River Hotel
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Streeterville, 13.6 km from Woodlawn
9.0 out of 10, Wonderful, (3438)
"Great hotel located in nice area."
United States
Robert
The price is ₹9,519
₹11,175 total
includes taxes & fees
15 Dec - 16 Dec
Hilton Chicago/Magnificent Mile Suites
Terrace/patio
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, (2257)
"Smooth check in and beautiful hotel"
United States
Monique
The price is ₹8,413
₹12,940 total
includes taxes & fees
23 Dec - 24 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (2947)
"Great location and great staff!!"
United States
lynne
The price is ₹7,559
₹8,874 total
includes taxes & fees
11 Dec - 12 Dec
Aloft Chicago Mag Mile
Property amenity
citizenM Chicago Downtown

citizenM Chicago Downtown

4.0 star property
Theatre District, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (4090)
"I enjoyed my stay with this hotel and would stay here again"
United States
Kim Leticia Terrelle
The price is ₹9,629
₹11,304 total
includes taxes & fees
14 Dec - 15 Dec
citizenM Chicago Downtown
Exterior
Hilton Chicago

Hilton Chicago

4.0 star property
The Loop, 10.7 km from Woodlawn
8.4 out of 10, Very good, (2352)
"We had a great stay and will be back again."
United States
Amber
The price is ₹10,257
₹14,682 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Chicago
Bar (on property)
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
8.4 out of 10, Very good, (4224)
"Great location. "
United States
Rodger
The price is ₹7,487
₹8,789 total
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
West Loop, 11.3 km from Woodlawn
8.4 out of 10, Very good, (1004)
"Amazing staff clean and secure hotel "
United States
Aniyah
The price is ₹9,089
₹11,750 total
includes taxes & fees
25 Dec - 26 Dec
Holiday Inn & Suites Chicago - Downtown by IHG
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, (2104)
"Would stay again. "
United States
Montroy
Silversmith Hotel Chicago Downtown
Exterior
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, (361)
"love this place definitely coming back !"
United States
Dayanara
The price is ₹5,782
₹6,787 total
includes taxes & fees
5 Jan - 6 Jan 2026
FOUND Hotel Chicago River North
American cuisine
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (1745)
"The location was great!!"
United States
Yvette
The price is ₹7,694
₹9,033 total
includes taxes & fees
14 Dec - 15 Dec
Crowne Plaza Chicago West Loop by IHG
Cocktail bar
Freehand Chicago

Freehand Chicago

4.0 star property
River North, 12.9 km from Woodlawn
8.0 out of 10, Very good, (2622)
"Great location "
United States
Stacy
The price is ₹5,653
₹8,221 total
includes taxes & fees
6 Jan - 7 Jan 2026
Freehand Chicago
Banquet hall
Congress Plaza Hotel

Congress Plaza Hotel

3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (9624)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
The price is ₹9,752
₹11,447 total
includes taxes & fees
2 Jan - 3 Jan 2026
Congress Plaza Hotel
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (2926)
"Everything was wonderful-Clean and comfortable beds and extremely good breakfast buffet! "
United States
Nita
The price is ₹8,910
₹12,995 total
includes taxes & fees
8 Dec - 9 Dec
Hotel Riu Plaza Chicago
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Theatre District, 11.7 km from Woodlawn
8.4 out of 10, Very good, (2118)
"Loved and enjoyed our stay"
United States
Luis
The price is ₹9,224
₹13,078 total
includes taxes & fees
28 Dec - 29 Dec
Palmer House a Hilton Hotel
Rooftop terrace
Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago

4.0 star property
Theatre District, 11.7 km from Woodlawn
9.0 out of 10, Wonderful, (2272)
"Awesome place to stay that was located in the middle of everything! "
United States
Denny
The price is ₹10,007
₹11,747 total
includes taxes & fees
21 Dec - 22 Dec
Hyatt Centric The Loop Chicago
Rooftop terrace
Best Western River North Hotel

Best Western River North Hotel

2.5 star property
River North, 13 km from Woodlawn
7.8 out of 10, Good, (1021)
"Staff was very friendly "
United States
david
The price is ₹7,675
₹9,009 total
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western River North Hotel
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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Where to stay in Woodlawn

Find the best Woodlawn areas for the activities you enjoy most.
Downtown Chicago featuring a city

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 - River North

Magnificent Mile

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

The Loop - Downtown featuring a river or creek

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.

Chicago which includes rides

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

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Everything was amazing, from the staff to the room, amenities simply perfect.!! "
TERESA 3-night trip
Posted 15 hours ago
Hyatt Regency Chicago

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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.