Hotels in Woodlawn

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

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, (63 reviews)
"Clean room "
United States
Pierre
The price is S$89
includes taxes & fees
14 May - 15 May
Best Motel By OYO Chicago I-90

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, (2,389 reviews)
"Beautiful property, great resturant on site, an the pool and spa was amazing."
United States
Tim
The price is S$274
includes taxes & fees
8 May - 9 May
Palmer House a Hilton Hotel

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, (2,463 reviews)
"Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. "
United States
Christopher
The price is S$386
includes taxes & fees
16 Apr - 17 Apr
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (3,832 reviews)
"The property was absolutely stunning and the staff was great."
United States
Pamela
The price is S$223
includes taxes & fees
19 Apr - 20 Apr
Hotel Riu Plaza Chicago

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, (2,686 reviews)
"Nice, quiet place to stay at, close to a lot of places to eat and to adventure out to."
United States
Kristin
The price is S$173
includes taxes & fees
26 Apr - 27 Apr
Best Western Grant Park Hotel

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, (547 reviews)
"Love this place. Kind of like a college dorm with community kitchen. Will stay there again. "
United States
William
The price is S$126
includes taxes & fees
27 Apr - 28 Apr
FOUND Hotel Chicago River North

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 12.9 km from Woodlawn
8.0 out of 10, Very good, (2,870 reviews)
"Great location, clean and decent sized room, staff was helpful and amenities are very convenient!"
United States
MaryJane
The price is S$140
includes taxes & fees
28 Apr - 29 Apr
Freehand Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 13.2 km from Woodlawn
8.6 out of 10, Excellent, (3,042 reviews)
"Excellent service, clean, comfortable, and a great location. "
United States
Lisa
The price is S$190
includes taxes & fees
27 Apr - 28 Apr
Warwick Allerton - Chicago

River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,090 reviews)
"Great location and nice hotel! "
United States
James
The price is S$179
includes taxes & fees
11 May - 12 May
River Hotel

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, (3,458 reviews)
"Wonderful hotel, friendly and accommodating staff! "
United States
Chevon
The price is S$157
includes taxes & fees
10 May - 11 May
Club Quarters Hotel, Central Loop, Chicago

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (3,180 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is S$193
includes taxes & fees
26 Apr - 27 Apr
Aloft Chicago Mag Mile

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (2,735 reviews)
"Super friendly staff and the room was incredible!"
United States
James
The price is S$338
includes taxes & fees
8 May - 9 May
Hilton Chicago

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Streeterville, 13 km from Woodlawn
8.4 out of 10, Very good, (1,889 reviews)
"Great location and a very high class hotel."
United States
Cornelius
The price is S$142
includes taxes & fees
19 Apr - 20 Apr
Hotel Saint Clair- Magnificent Mile

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (10,142 reviews)
"Clean room, nice hotel, nice staff"
United States
Melanie
The price is S$184
includes taxes & fees
26 Apr - 27 Apr
Congress Plaza Hotel

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, (1,370 reviews)
"The staff is so amazing, and accommodating, Cristin and David are amazing when helping! The area is so fun and so close to so many shopping centers and great places to eat. In a very convenient spot for traveling in !! "
United States
Sonovia
The price is S$170
includes taxes & fees
28 Apr - 29 Apr
The Chicago Hotel Collection Ambassador Gold Coast

Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 10.6 km from Woodlawn
8.8 out of 10, Excellent, (1,016 reviews)
"Great views close to museums and great restaurants "
United States
Blanca L
The price is S$215
includes taxes & fees
10 May - 11 May
Le Méridien Essex Chicago

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, (1,954 reviews)
"The staff here were extremely friendly and made the stay more enjoyable "
United States
Trinity
The price is S$176
includes taxes & fees
27 Apr - 28 Apr
Hilton Garden Inn Chicago Downtown South Loop

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, (2,308 reviews)
"Great Hotel, location close to all attractions, clean, perfect breakfast "
United States
Sheila
The price is S$201
includes taxes & fees
26 Apr - 27 Apr
Homewood Suites by Hilton Chicago Downtown South Loop

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, (2,187 reviews)
"Staff were always friendly and professional. Very clean and neat space. Shower was a little cramped and outdated but clean. Views are nice. Laundry room is super convenient and affordable. Location is extremely walkable, in the heart of Chicago. My only complaint was that the parking was a few blocks around the corner. But I had free parking and for downtown Chicago it wasn’t bad, just cold in my case. Definitely would recommend this hotel"
United States
Darianne
The price is S$191
includes taxes & fees
11 May - 12 May
Club Quarters Hotel Wacker at Michigan, Chicago

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.6 km from Woodlawn
8.6 out of 10, Excellent, (2,074 reviews)
"Great hotel in a great location."
United States
Ben
The price is S$173
includes taxes & fees
26 Apr - 27 Apr
Central Loop 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.

Where to stay in Woodlawn

Find the best Woodlawn areas for the activities you enjoy most. Learn more about Woodlawn
Learn more about Woodlawn

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.

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.

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.

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 51 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