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Woodlawn Hotels, Chicago

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8 Oct - 9 Oct
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9 Oct - 10 Oct
This weekend
10 Oct - 12 Oct
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17 Oct - 19 Oct

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4397 Cheap Hotels in Woodlawn - Specials, Reviews, & Last Minute Deals

Best Motel By OYO Chicago I-90
Hallway

Best Motel By OYO Chicago I-90

2.0 star property
3.4 out of 10, (45)
"Easy, safe parking "
The price is AU$164
includes taxes & fees
9 Oct - 10 Oct
Best Motel By OYO Chicago I-90
Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (3068)
"The hotel has a restaurant on the first floor with patio seating and great views."
The price is AU$214
includes taxes & fees
3 Nov - 4 Nov
Eurostars Magnificent Mile
River Hotel
Reception

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4724)
"Staff friendly and helpful..and accommodations just right..great location! "
The price is AU$220
includes taxes & fees
6 Nov - 7 Nov
River Hotel
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3923)
"Great place to stay. "
The price is AU$292
includes taxes & fees
4 Nov - 5 Nov
citizenM Chicago Downtown
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2079)
"Great hotel"
The price is AU$284
includes taxes & fees
2 Nov - 3 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2178)
"Great hotel "
The price is AU$391
includes taxes & fees
2 Nov - 3 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
Aloft Chicago Mag Mile
Cocktail bar

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2852)
"Had a great stay!"
The price is AU$262
includes taxes & fees
2 Nov - 3 Nov
Aloft Chicago Mag Mile
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (3049)
"Our stay was great"
The price is AU$256
includes taxes & fees
3 Nov - 4 Nov
Hilton Chicago/Magnificent Mile Suites
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (9346)
"Beautiful hotel!"
Congress Plaza Hotel
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2428)
"Great walkable location to all the sights! "
The price is AU$185
includes taxes & fees
4 Nov - 5 Nov
Freehand Chicago
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very good, (4049)
"We definitely will stay there again place was very nice "
The price is AU$312
includes taxes & fees
20 Oct - 21 Oct
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (2249)
"We loved this hotel it was beautiful and convenient . "
The price is AU$371
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very good, (269)
"Perfect location! Tons of restaurants and shopping nearby! "
The price is AU$174
includes taxes & fees
4 Nov - 5 Nov
FOUND Hotel Chicago River North
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2563)
"Great place to stay "
The price is AU$327
includes taxes & fees
5 Nov - 6 Nov
Hotel Riu Plaza Chicago
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1020)
"Great stay"
The price is AU$226
includes taxes & fees
2 Nov - 3 Nov
Best Western River North Hotel
Hyatt Centric The Loop Chicago
Rooftop terrace

Hyatt Centric The Loop Chicago

4.0 star property
9.0 out of 10, Wonderful, (2172)
"It was an amazing stay!"
The price is AU$368
includes taxes & fees
23 Oct - 24 Oct
Hyatt Centric The Loop Chicago
Crowne Plaza Chicago West Loop by IHG
American cuisine

Crowne Plaza Chicago West Loop by IHG

3.5 star property
9.0 out of 10, Wonderful, (1580)
"Excellent breakfast and room was quiet and clean. "
The price is AU$234
includes taxes & fees
2 Nov - 3 Nov
Crowne Plaza Chicago West Loop by IHG
Warwick Allerton - Chicago
Lobby sitting area

Warwick Allerton - Chicago

4.0 star property
8.4 out of 10, Very good, (2903)
"Great location, friendly staff."
The price is AU$201
includes taxes & fees
3 Nov - 4 Nov
Warwick Allerton - Chicago
voco Chicago Downtown - Riverwalk by IHG
Bar (on property)

voco Chicago Downtown - Riverwalk by IHG

3.5 star property
8.8 out of 10, Excellent, (3194)
"Great stay "
The price is AU$298
includes taxes & fees
2 Nov - 3 Nov
voco Chicago Downtown - Riverwalk by IHG
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.4 out of 10, Good, (2394)
"Comfortable bed, bright room, good shower, very accessible location."
The price is AU$192
includes taxes & fees
4 Nov - 5 Nov
Travelodge by Wyndham Downtown 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.
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Our guide on 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 which includes a river or creek

The Loop

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

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 showing a city and modern architecture

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

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Excellent
"Great shape! "
Kate 2-night trip
Posted 23 hours ago
Sable at Navy Pier Chicago, Curio Collection by Hilton

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 45 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?
Ready to get out and explore the city? Cottage Grove Station is the closest metro station. To venture out of town, take a train from Chicago 63rd Street Station.

Explore a world of travel with Expedia

Explore a world of travel with Expedia