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Woodlawn Hotels, Chicago

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4 Nov - 5 Nov
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5 Nov - 6 Nov
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7 Nov - 9 Nov
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14 Nov - 16 Nov

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4516 Cheap Hotels in Woodlawn - Specials, Reviews, & Last Minute Deals

Hallway
Best Motel By OYO Chicago I-90
Best Motel By OYO Chicago I-90
2.0 star property
3.4 out of 10, (47)
"Easy, safe parking "
United States
Ramon
The price is AU$113
includes taxes & fees
4 Dec - 5 Dec
Best Motel By OYO Chicago I-90
Reception
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4.0 star property
9.0 out of 10, Wonderful, (3092)
"Awesome location and excellent service, the staff was great!"
United States
Salvador
The price is AU$194
includes taxes & fees
9 Nov - 10 Nov
Eurostars Magnificent Mile
Reception
River Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (4777)
"Beautiful hotel. Had a nice stay"
United States
Esther
The price is AU$173
includes taxes & fees
23 Nov - 24 Nov
River Hotel
Outdoor pool, pool cabanas (surcharge), pool umbrellas
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (2129)
"Convenient location, over all cleanliness and staff was exceptional."
United States
AMANDA
The price is AU$185
includes taxes & fees
23 Nov - 24 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Terrace/patio
citizenM Chicago Downtown
citizenM Chicago Downtown
4.0 star property
9.2 out of 10, Wonderful, (4056)
"Clean room, amazing staff, everything was in walking distance. Definitely worth the stay! "
United States
Shakeina
The price is AU$205
includes taxes & fees
19 Nov - 20 Nov
citizenM Chicago Downtown
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4 out of 10, Exceptional, (2244)
"Room was spotless…staff was great!"
United States
Tamika
The price is AU$227
includes taxes & fees
25 Nov - 26 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
Cocktail bar
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2878)
"Clean room and loved the atmosphere"
United States
Madison
The price is AU$194
includes taxes & fees
23 Nov - 24 Nov
Aloft Chicago Mag Mile
Ballroom
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 star property
9.0 out of 10, Wonderful, (3228)
"Overall it was a great place to stay."
United States
Edward
The price is AU$182
includes taxes & fees
17 Nov - 18 Nov
Hilton Chicago/Magnificent Mile Suites
Cocktail bar
Freehand Chicago
Freehand Chicago
4.0 star property
8.0 out of 10, Very good, (2565)
"Location was excellent would stay there again"
United States
Julio
The price is AU$148
includes taxes & fees
12 Nov - 13 Nov
Freehand Chicago
Banquet hall
Congress Plaza Hotel
Congress Plaza Hotel
3.5 star property
8.0 out of 10, Very good, (9677)
"The location and view was great. "
United States
Jacqueline
The price is AU$370
includes taxes & fees
6 Nov - 7 Nov
Congress Plaza Hotel
Exterior
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
8.4 out of 10, Very good, (4137)
"Clean rooms and friendly staff"
United States
Jeffrey
The price is AU$176
includes taxes & fees
25 Nov - 26 Nov
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior
Hilton Chicago
Hilton Chicago
4.0 star property
8.4 out of 10, Very good, (2281)
"Great Hotel"
United States
Luz
The price is AU$249
includes taxes & fees
24 Nov - 25 Nov
Hilton Chicago
Front of property
Hotel Riu Plaza Chicago
Hotel Riu Plaza Chicago
4.0 star property
9.4 out of 10, Exceptional, (2709)
"Great place to stay "
United States
Larry William
The price is AU$290
includes taxes & fees
4 Dec - 5 Dec
Hotel Riu Plaza Chicago
Exterior
FOUND Hotel Chicago River North
FOUND Hotel Chicago River North
2.0 star property
8.2 out of 10, Very good, (302)
"Perfect location! Tons of restaurants and shopping nearby! "
United States
MaryJane
The price is AU$137
includes taxes & fees
11 Nov - 12 Nov
FOUND Hotel Chicago River North
American cuisine
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 star property
9.0 out of 10, Wonderful, (1651)
"Great hotel and amenities "
United States
Adrienne
The price is AU$183
includes taxes & fees
23 Nov - 24 Nov
Crowne Plaza Chicago West Loop by IHG
Rooftop terrace
Best Western River North Hotel
Best Western River North Hotel
2.5 star property
7.8 out of 10, Good, (1010)
"It was a great stay"
United States
Brooklynn
The price is AU$182
includes taxes & fees
23 Nov - 24 Nov
Best Western River North Hotel
Rooftop terrace
Hyatt Centric The Loop Chicago
Hyatt Centric The Loop Chicago
4.0 star property
9.0 out of 10, Wonderful, (2232)
"Probably my favorite place to stay in the Loop."
United States
Robert
The price is AU$222
includes taxes & fees
25 Nov - 26 Nov
Hyatt Centric The Loop Chicago
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
3.0 star property
8.4 out of 10, Very good, (1008)
"Staff was very friendly The rooftop pool was really nice. "
United States
angela
The price is AU$230
includes taxes & fees
9 Nov - 10 Nov
Holiday Inn & Suites Chicago - Downtown by IHG
Lobby
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago Downtown
4.0 star property
9.4 out of 10, Exceptional, (2039)
"Staff was always nice, rooms were clean and bathrooms were huge. "
United States
Dan
The price is AU$350
includes taxes & fees
9 Nov - 10 Nov
Silversmith Hotel Chicago Downtown
Restaurant
Best Western Grant Park Hotel
Best Western Grant Park Hotel
2.5 star property
8.2 out of 10, Very good, (2619)
"Great hotel! "
United States
Cynthia
The price is AU$151
includes taxes & fees
10 Nov - 11 Nov
Best Western Grant Park 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.
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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

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"Everything was fantastic!"
Megan 1-night trip
Posted 1 day ago
citizenM Chicago Downtown

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 46 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.

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