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Woodlawn Hotels, Chicago

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6 Sept - 7 Sept
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7 Sept - 8 Sept
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12 Sept - 14 Sept
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19 Sept - 21 Sept

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4437 Cheap Hotels in Woodlawn - Specials, Reviews, & Last Minute Deals

Our top choices for Woodlawn hotels

Best Motel By OYO Chicago I-90
Hallway

Best Motel By OYO Chicago I-90

2.0 star property
3.4 out of 10, (40)
"Easy, safe parking "
The price is AU$139
includes taxes & fees
7 Sept - 8 Sept
Best Motel By OYO Chicago I-90
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, pool loungers

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2016)
"Overall a nice place to stay."
The price is AU$299
includes taxes & fees
21 Sept - 22 Sept
DoubleTree by Hilton Chicago - Magnificent Mile
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3727)
"Great place to stay "
The price is AU$341
includes taxes & fees
22 Sept - 23 Sept
citizenM Chicago Downtown
Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3043)
"Great stay!"
The price is AU$325
includes taxes & fees
5 Oct - 6 Oct
Eurostars 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, (2112)
"Great place to stay!"
The price is AU$401
includes taxes & fees
14 Sept - 15 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
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, (3817)
"Great place to stay "
The price is AU$291
includes taxes & fees
14 Sept - 15 Sept
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2799)
"Great hotel and location"
The price is AU$288
includes taxes & fees
22 Sept - 23 Sept
Hilton Chicago/Magnificent Mile Suites
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (9068)
"Great value for the location "
The price is AU$354
includes taxes & fees
4 Oct - 5 Oct
Congress Plaza Hotel
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2275)
"Nice place to stay!"
The price is AU$211
includes taxes & fees
23 Sept - 24 Sept
Freehand Chicago
Aloft Chicago Mag Mile
Meeting facility

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2810)
"Close to everything, easy check-in/out and friendly staff!"
The price is AU$265
includes taxes & fees
14 Sept - 15 Sept
Aloft Chicago Mag Mile
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (2167)
"Amazing stay and great location…"
The price is AU$374
includes taxes & fees
25 Sept - 26 Sept
Hilton Chicago
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very good, (226)
"Great place "
The price is AU$228
includes taxes & fees
23 Sept - 24 Sept
FOUND Hotel Chicago River North
Holiday Inn & Suites Chicago - Downtown by IHG
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
8.4 out of 10, Very good, (1010)
"Staff was very friendly The rooftop pool was really nice. "
The price is AU$321
includes taxes & fees
5 Oct - 6 Oct
Holiday Inn & Suites Chicago - Downtown by IHG
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1030)
"It was a great stay"
The price is AU$257
includes taxes & fees
2 Oct - 3 Oct
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, (2086)
"Property was great, very clean and friendly staff. The location is wonderful. Will definitely stay here again. "
The price is AU$385
includes taxes & fees
12 Sept - 13 Sept
Hyatt Centric The Loop Chicago
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2395)
"Enjoyed our stay "
The price is AU$385
includes taxes & fees
22 Sept - 23 Sept
Hotel Riu Plaza Chicago
Palmer House a Hilton Hotel
Ballroom

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very good, (1926)
"Nice stay"
The price is AU$409
includes taxes & fees
25 Sept - 26 Sept
Palmer House a Hilton Hotel
La Quinta Inn & Suites by Wyndham Chicago Downtown
Exterior

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
8.6 out of 10, Excellent, (2529)
"Had a wonderful stay here and staff was super friendly!"
The price is AU$364
includes taxes & fees
14 Sept - 15 Sept
La Quinta Inn & Suites by Wyndham Chicago Downtown
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, (1455)
"Great place to stay. "
The price is AU$347
includes taxes & fees
28 Sept - 29 Sept
Crowne Plaza Chicago West Loop by IHG
Hyatt Regency Chicago
2 bars/lounges

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3322)
"The stay was wonderful. "
The price is AU$467
includes taxes & fees
21 Sept - 22 Sept
Hyatt Regency 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

2 out of top 10 points of interest in this area

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

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 42 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.