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Woodlawn Hotels, Chicago

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3 Oct - 4 Oct
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4409 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 NZ$158
includes taxes & fees
7 Oct - 8 Oct
Best Motel By OYO Chicago I-90
River Hotel
Reception

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4705)
"Staff friendly and helpful..and accommodations just right..great location! "
The price is NZ$381
includes taxes & fees
5 Oct - 6 Oct
River Hotel
Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3057)
"Perfect location, walkable to many restaurants and shops"
The price is NZ$221
includes taxes & fees
3 Nov - 4 Nov
Eurostars Magnificent Mile
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, (2076)
"Great hotel"
The price is NZ$321
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, (2164)
"Great hotel "
The price is NZ$435
includes taxes & fees
2 Nov - 3 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (3899)
"Absolutely loved this hotel and location. "
The price is NZ$349
includes taxes & fees
4 Nov - 5 Nov
citizenM Chicago Downtown
Aloft Chicago Mag Mile
Cocktail bar

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2844)
"Had a great stay!"
The price is NZ$290
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, (3013)
"Enjoyed our stay"
The price is NZ$291
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, (9282)
"Beautiful hotel!"
Congress Plaza Hotel
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2408)
"Great walkable location to all the sights! "
The price is NZ$253
includes taxes & fees
27 Oct - 28 Oct
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, (4023)
"We definitely will stay there again place was very nice "
The price is NZ$361
includes taxes & fees
19 Oct - 20 Oct
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (2237)
"Very nice hotel "
The price is NZ$421
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1017)
"Great stay"
The price is NZ$255
includes taxes & fees
2 Nov - 3 Nov
Best Western River North Hotel
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2528)
"Location is great and the breakfast buffet is amazing"
The price is NZ$371
includes taxes & fees
3 Nov - 4 Nov
Hotel Riu Plaza Chicago
Hyatt Centric The Loop Chicago
Rooftop terrace

Hyatt Centric The Loop Chicago

4.0 star property
9.0 out of 10, Wonderful, (2157)
"The hotel was quiet and clean and restaurant was right next door in addition to inside the hotel"
The price is NZ$450
includes taxes & fees
30 Oct - 31 Oct
Hyatt Centric The Loop Chicago
Warwick Allerton - Chicago
Lobby sitting area

Warwick Allerton - Chicago

4.0 star property
8.4 out of 10, Very good, (2896)
"Great location, friendly staff."
The price is NZ$228
includes taxes & fees
3 Nov - 4 Nov
Warwick Allerton - 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, (1567)
"Hotel was very comfortable and I felt very safe during my entire stay. "
The price is NZ$295
includes taxes & fees
19 Oct - 20 Oct
Crowne Plaza Chicago West Loop by IHG
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, (2561)
"Good place to stay"
The price is NZ$350
includes taxes & fees
2 Nov - 3 Nov
La Quinta Inn & Suites by Wyndham Chicago Downtown
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2377)
"Comfortable bed, bright room, good shower, very accessible location."
The price is NZ$228
includes taxes & fees
4 Nov - 5 Nov
Travelodge by Wyndham Downtown 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, (3175)
"Great stay "
The price is NZ$422
includes taxes & fees
5 Oct - 6 Oct
voco Chicago Downtown - Riverwalk by IHG
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

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

The Loop - Downtown which includes a river or creek

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.

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

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"Very comfortable stay, excellent location. "
Andrea 3-night trip
Posted 11 hours ago
Hilton Garden Inn Chicago Downtown/Magnificent Mile

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 44 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.