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

Woodlawn hotels in Chicago

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Check prices for these dates

Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov

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Our top choices for Woodlawn hotels

A room with large windows, a wooden floor, and a built-in air conditioning unit.

1. Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.5 star property
Woodlawn
3.4 out of 10, (156 reviews)
"A/c working, friendly staff, free parking but messy sheets and a baby mouse in the room"
United States
Saul
The price is HK$646
HK$758 total
includes taxes & fees
1 Nov - 2 Nov
Best Motel By OYO Chicago I-90
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

2. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (3,430 reviews)
"Friendly staff, great location"
Canada
Anna
The price is HK$1,327
HK$1,808 total
includes taxes & fees
13 Nov - 14 Nov
Hilton Chicago
A modern kitchen with a large window, a dining area, and a view of the sea.

3. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
The Loop, 10.4 km from Woodlawn
8.8 out of 10, Excellent, (2,524 reviews)
"Clean room great breakfast loved the pool"
United States
Cynthia
The price is HK$1,127
HK$1,340 total
includes taxes & fees
10 Nov - 11 Nov
Homewood Suites by Hilton Chicago Downtown South Loop
The Intercontinental hotel facade with a large American flag and a floral display.

4. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Magnificent Mile, 12.7 km from Woodlawn
9.2 out of 10, Wonderful, (3,385 reviews)
"Great hotel"
United States
Said Lopez
The price is HK$1,664
HK$2,253 total
includes taxes & fees
31 Oct - 1 Nov
InterContinental Chicago Magnificent Mile by IHG
A spacious bar area with high ceilings and large windows, offering views of a cityscape.

5. Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3,512 reviews)
"The hotel was beautiful, great location"
United States
Addison
The price is HK$1,868
HK$2,501 total
includes taxes & fees
31 Oct - 1 Nov
Hyatt Regency Chicago
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

6. 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, (3,875 reviews)
"It was a very nice stay! We enjoyed the hotel The views were amazing"
United States
James
The price is HK$1,734
HK$2,295 total
includes taxes & fees
15 Nov - 16 Nov
LondonHouse Chicago, Curio Collection by Hilton
A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

7. L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 12.3 km from Woodlawn
9.6 out of 10, Exceptional, (5,047 reviews)
"A fantastic A+ location in a well kept, boutique type hotel."
United States
Jeffrey Thomas
The price is HK$1,290
HK$1,534 total
includes taxes & fees
1 Nov - 2 Nov
L7 Chicago by LOTTE
A modern interior with a bar area, seating, and decorative wooden panels.

8. Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 10.3 km from Woodlawn
8.2 out of 10, Very good, (2,750 reviews)
"Clean room, friendly staff, and convenient location."
Canada
Colin
The price is HK$840
HK$999 total
includes taxes & fees
10 Nov - 11 Nov
Best Western Grant Park Hotel
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

9. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 10.4 km from Woodlawn
8.8 out of 10, Excellent, (2,192 reviews)
"Great place to stay at"
United States
Aran
The price is HK$961
HK$1,142 total
includes taxes & fees
11 Nov - 12 Nov
Hilton Garden Inn Chicago Downtown South Loop
A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.

10. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 11.1 km from Woodlawn
9.6 out of 10, Exceptional, (1,220 reviews)
"Great location!"
United States
Mario
The price is HK$1,348
HK$1,603 total
includes taxes & fees
4 Nov - 5 Nov
Hilton Vacation Club Hotel Blake Chicago
A multi-story hotel with a prominent sign reading "Crowne Plaza."

11. 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, (2,736 reviews)
"Nice hotel and location was perfect."
United States
Chriselda
The price is HK$1,261
HK$1,499 total
includes taxes & fees
1 Nov - 2 Nov
Crowne Plaza Chicago West Loop by IHG
An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

12. 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, (2,707 reviews)
"Beautiful hotel with wonderful staff!"
United States
Christy
The price is HK$1,494
HK$2,010 total
includes taxes & fees
31 Oct - 1 Nov
Palmer House a Hilton Hotel
The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

13. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (5,540 reviews)
"Good location, nice room and buffet breakfast!"
United Kingdom
Suki
The price is HK$1,390
HK$1,876 total
includes taxes & fees
10 Nov - 11 Nov
Hotel Riu Plaza Chicago
A high-rise hotel with a prominent curved glass facade, multiple floors, and a visible "EMBASSY" sign.

14. 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
8.4 out of 10, Very good, (3,013 reviews)
"Great location and staff were amazing to us!"
United States
jaimie
The price is HK$1,127
HK$1,571 total
includes taxes & fees
1 Nov - 2 Nov
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

15. Hyatt Place Chicago/River North

Hyatt Place Chicago/River North
3.5 star property
River North, 12.8 km from Woodlawn
9.2 out of 10, Wonderful, (1,917 reviews)
"Great location!"
United States
Nilofar
The price is HK$1,365
HK$1,623 total
includes taxes & fees
12 Nov - 13 Nov
Hyatt Place Chicago/River North
A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

16. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
12.7 km from Woodlawn
9.0 out of 10, Wonderful, (1,308 reviews)
"Location was amazing. Loved the outdoor market in walking distance"
United States
Georgianna
The price is HK$1,530
HK$1,819 total
includes taxes & fees
1 Nov - 2 Nov
Hyatt House Chicago/West Loop-Fulton Market
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

17. 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, (2,591 reviews)
"Nice stay for the weekend."
United States
Poua
The price is HK$1,007
HK$1,198 total
includes taxes & fees
1 Nov - 2 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
An outdoor seating area with a glass table, orange cushions, and potted plants.

18. Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 12.4 km from Woodlawn
8.6 out of 10, Excellent, (1,864 reviews)
"Loved our stay! In a convenient location."
United States
Stacie
The price is HK$1,718
HK$2,323 total
includes taxes & fees
13 Nov - 14 Nov
Sheraton Grand Chicago Riverwalk
A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

19. Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (3,328 reviews)
"nice chic clean place to stay near navy pier"
United States
Jonathan M
The price is HK$1,136
HK$1,350 total
includes taxes & fees
1 Nov - 2 Nov
Aloft by Marriott Chicago Mag Mile
A modern building with a black facade and multiple windows. There is a sign for Hilton Garden Inn and a flagpole with flags.

20. Hilton Garden Inn Chicago Downtown Riverwalk

Hilton Garden Inn Chicago Downtown Riverwalk
3.0 star property
The Loop, 12.3 km from Woodlawn
9.0 out of 10, Wonderful, (2,205 reviews)
"Great stay great stay great location"
United States
Brittney
The price is HK$1,281
HK$1,523 total
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Chicago Downtown Riverwalk
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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Hotels recommended for families in Woodlawn

A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,430)
The price is HK$1,327
HK$1,808 total
includes taxes & fees
13 Nov - 14 Nov
Hilton Chicago

Where to stay in Woodlawn

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

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 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

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

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

The Loop

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

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

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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"We stayed at the Congress for a Bears game. We selected it based on price and proximity to Soldier Field. The price was incredibly reasonable, so I was a bit concerned about the quality and cleanliness of the room and hotel prior to checking in. We were more than pleased with our room and the hotel overall and feel it was great value for our money. The room was very clean and had been updated quite recently. It was roomie in both the room itself and the bathroom. We also appreciated the amenities in the room, including a coffee maker, refrigerator, a large, walk-in closet, plenty of drawer storage for clothes and extra seating and table. It is also near do much in the city, so it’s a great place to stay. The only issue that I had is I wish the TV had been a bit larger. But other than that, I would highly recommend the Congress."
Dean 2-night trip
Posted 15 hours ago
Congress Plaza Hotel

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. Obama Presidential Center 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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