613-28 Japanese Island Jackson Park Chicago

Woodlawn Hotels, Chicago

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
12 Jun - 14 Jun
Next weekend
19 Jun - 21 Jun

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Woodlawn hotels

Room, 2 Double Beds, Smoking | Bathroom

1. Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.0 star property
Woodlawn
3.6 out of 10, (83 reviews)
"This is not a good place."
United States
Dinesh Kumar
The price is NZ$134
includes taxes & fees
9 July - 10 July
Best Motel By OYO Chicago I-90
Terrace/patio

2. 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, (2,534 reviews)
"Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"
United States
Deborah
The price is NZ$555
includes taxes & fees
1 July - 2 July
Sable at Navy Pier Chicago, Curio Collection by Hilton
Exterior

3. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (2,850 reviews)
"great hotel and excellent to stay"
United States
Ruben
The price is NZ$485
includes taxes & fees
6 July - 7 July
Hilton Chicago
Lobby

4. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (10,226 reviews)
"Great stay thanks"
United States
Felipa
The price is NZ$278
includes taxes & fees
29 June - 30 June
Congress Plaza Hotel
Lobby

5. 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, (2,241 reviews)
"Great location"
United States
Gabino
The price is NZ$285
includes taxes & fees
5 July - 6 July
Silversmith Hotel Chicago Downtown
2 bars/lounges

6. Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3,506 reviews)
"Staff was great."
United States
Marianne
The price is NZ$477
includes taxes & fees
5 July - 6 July
Hyatt Regency Chicago
Breakfast and dinner served

7. Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Streeterville, 13.1 km from Woodlawn
9.2 out of 10, Wonderful, (1,797 reviews)
"Great place at a great location."
United States
Alejandro
The price is NZ$383
includes taxes & fees
1 July - 2 July
Omni Chicago Hotel
Indoor wedding

8. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,375 reviews)
"Nice Hotel, rooms are clean , the best for us was the location, i would recommend"
United States
Sergio
The price is NZ$419
includes taxes & fees
6 July - 7 July
Swissotel - Chicago
2 bars/lounges

9. Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 12.4 km from Woodlawn
8.6 out of 10, Excellent, (1,659 reviews)
"Excellent location."
United States
Mirna
The price is NZ$538
includes taxes & fees
7 July - 8 July
Sheraton Grand Chicago Riverwalk
Front of property

10. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (4,396 reviews)
"The breakfast, location, and staff were amazing."
United States
Corey
The price is NZ$376
includes taxes & fees
30 June - 1 July
Hotel Riu Plaza Chicago
View from property

11. The Blackstone, Autograph Collection

The Blackstone, Autograph Collection
4.0 star property
The Loop, 10.8 km from Woodlawn
9.0 out of 10, Wonderful, (1,008 reviews)
"Great location, clean hotel, and very accommodating staff."
United States
Neydee
The price is NZ$368
includes taxes & fees
1 July - 2 July
The Blackstone, Autograph Collection
2 restaurants; breakfast, lunch and dinner served

12. 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, (3,735 reviews)
"Great location, excellent room and amenities proactively attentive staff."
United States
Robert
The price is NZ$515
includes taxes & fees
21 June - 22 June
LondonHouse Chicago, Curio Collection by Hilton
Exterior

13. 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, (4,397 reviews)
"Great stay!"
United States
Avradita
The price is NZ$328
includes taxes & fees
7 July - 8 July
Hilton Chicago/Magnificent Mile Suites
Reception hall

14. Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13.1 km from Woodlawn
9.0 out of 10, Wonderful, (3,631 reviews)
"Had an amazing stay here!"
United States
Audrey
The price is NZ$327
includes taxes & fees
1 July - 2 July
Eurostars Magnificent Mile
Room service – dining

15. The Wade

The Wade
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.4 out of 10, Very good, (1,852 reviews)
"Excellent location, clean modern rooms."
United States
Molly
The price is NZ$399
includes taxes & fees
1 July - 2 July
The Wade
Exterior

16. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
The Loop, 11.1 km from Woodlawn
9.6 out of 10, Exceptional, (1,253 reviews)
"Overall comfortable stay and easy access by walk to downtown and all other places in the city."
United States
raghu
The price is NZ$342
includes taxes & fees
5 July - 6 July
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Interior detail

17. 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, (1,087 reviews)
"Such a lovely hotel with a beautiful, excellent staff, and lots of character!"
United States
Debby
The price is NZ$336
includes taxes & fees
6 July - 7 July
Staypineapple, An Iconic Hotel, The Loop
Bar (on property)

18. The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 13.6 km from Woodlawn
8.4 out of 10, Very good, (3,935 reviews)
"Overall a great stay, staff was friendly and bed was comfy."
United States
Meghan
The price is NZ$285
includes taxes & fees
30 June - 1 July
The Whitehall Hotel, BW Premier Collection
Exterior

19. Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 13.2 km from Woodlawn
8.6 out of 10, Excellent, (3,052 reviews)
"Great location, historic charm, friendly and helpful staff."
United States
Peter Anthony
The price is NZ$352
includes taxes & fees
5 July - 6 July
Warwick Allerton - Chicago
Exterior

20. Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.1 km from Woodlawn
9.4 out of 10, Exceptional, (2,132 reviews)
"Excellent location and welcoming staff."
United States
Tammy
The price is NZ$420
includes taxes & fees
2 July - 3 July
Arlo 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.
View all properties

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

An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

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.

Panoramic view of Lincoln Park and the Chicago skyline.

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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"The restaurant was not open very often. Nowhere to have a drink or buy snacks or drinks."
Leslie Ann 3-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast

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 47 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.

Explore a world of travel with Expedia