Woodlawn Hotels, Chicago

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Check prices for these dates

Next weekend
29 May - 31 May
In two weeks
5 Jun - 7 Jun

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Our top choices for Woodlawn hotels

Lobby

Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.0 star property
Woodlawn
3.8 out of 10, (70 reviews)
"Parking was easy. Just a sign in"
United States
David
The price is NZ$133
includes taxes & fees
23 June - 24 June
Best Motel By OYO Chicago I-90
Terrace/patio

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, (2,511 reviews)
"I loved it here and will definitely stay again."
United States
Gina
The price is NZ$498
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton
Room service – dining

The Wade

The Wade
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.4 out of 10, Very good, (1,841 reviews)
"Excellent location, clean modern rooms."
United States
Molly
The price is NZ$327
includes taxes & fees
25 May - 26 May
The Wade
2 bars/lounges

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 12.4 km from Woodlawn
8.6 out of 10, Excellent, (1,630 reviews)
"Beautiful views"
United States
Dominique
The price is NZ$663
includes taxes & fees
14 June - 15 June
Sheraton Grand Chicago Riverwalk
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,339 reviews)
"Great location!"
United States
Maria
The price is NZ$463
includes taxes & fees
27 May - 28 May
Swissotel - Chicago
Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 12.8 km from Woodlawn
8.8 out of 10, Excellent, (2,485 reviews)
"This is a beautiful hotel and the location was perfect."
United States
Felisha
The price is NZ$344
includes taxes & fees
25 May - 26 May
DoubleTree by Hilton Chicago - Magnificent Mile
Exterior

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 12.7 km from Woodlawn
8.2 out of 10, Very good, (2,850 reviews)
"Breakfast was excellent."
United States
Janine
The price is NZ$394
includes taxes & fees
27 May - 28 May
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Lunch and dinner served

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
12.2 km from Woodlawn
8.6 out of 10, Excellent, (1,944 reviews)
"Great Hotel "
United States
Dylan
The price is NZ$478
includes taxes & fees
25 May - 26 May
Radisson Blu Aqua Hotel Chicago
Executive lounge

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 12.1 km from Woodlawn
8.8 out of 10, Excellent, (2,166 reviews)
"Great place"
United States
JOSE
The price is NZ$401
includes taxes & fees
25 May - 26 May
Fairmont Chicago at Millennium Park
Lobby

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (3,243 reviews)
"Nice place to stay"
United States
Jimmie
The price is NZ$335
includes taxes & fees
27 May - 28 May
Aloft by Marriott Chicago Mag Mile
Bar (on property)

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.8 out of 10, Excellent, (1,272 reviews)
"Happy with our stay!"
United States
Jennifer
The price is NZ$251
includes taxes & fees
25 May - 26 May
Ivy Boutique Hotel
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Streeterville, 13.7 km from Woodlawn
8.6 out of 10, Excellent, (2,467 reviews)
"Perfect location, very comfortable rooms, friendly staff."
United States
Annabelle
The price is NZ$311
includes taxes & fees
25 May - 26 May
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Suite, Multiple Beds, Hearing Accessible | Lounge

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
9.0 out of 10, Wonderful, (1,002 reviews)
"All around great stay. "
United States
Nicholas
The price is NZ$262
includes taxes & fees
25 May - 26 May
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Exterior

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 13.6 km from Woodlawn
9.0 out of 10, Wonderful, (4,335 reviews)
"Beautiful Hotel great location"
United States
Nereida
The price is NZ$364
includes taxes & fees
26 May - 27 May
Hilton Chicago/Magnificent Mile Suites
Shopping centre

Millennium Hotel Knickerbocker Chicago

Millennium Hotel Knickerbocker Chicago
4.0 star property
Streeterville, 13.6 km from Woodlawn
8.6 out of 10, Excellent, (1,977 reviews)
"Loved everything including location and food options. Great hotel. "
United States
Eileen
The price is NZ$333
includes taxes & fees
27 May - 28 May
Millennium Hotel Knickerbocker Chicago
2 bars/lounges

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3,493 reviews)
"Very good place to stay. I really liked the lobby — it’s very spacious. The lobby design is also very open and artistic."
Canada
Tong
The price is NZ$547
includes taxes & fees
26 May - 27 May
Hyatt Regency Chicago
Exterior

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Streeterville, 13 km from Woodlawn
9.0 out of 10, Wonderful, (1,095 reviews)
"Great stay!"
United States
Milo
The price is NZ$455
includes taxes & fees
25 May - 26 May
Hyatt Centric Chicago Magnificent Mile
Premium bedding, in-room safe, desk, blackout curtains

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
9.0 out of 10, Wonderful, (1,903 reviews)
"Great Place to stay while in Chicago."
United States
Stacy
The price is NZ$319
includes taxes & fees
25 May - 26 May
Courtyard by Marriott Chicago Magnificent Mile
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 13.2 km from Woodlawn
7.8 out of 10, Good, (1,466 reviews)
"Great stay"
United States
Ontario
The price is NZ$262
includes taxes & fees
27 May - 28 May
The Chicago Hotel Collection - Magnificent Mile
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (4,227 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is NZ$535
includes taxes & fees
16 June - 17 June
Hotel Riu Plaza 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

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

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

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.

Panoramic view of Lincoln Park and the Chicago skyline.

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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4/10 Poor
"First room we got was not clean, they then changed us to another room and the air conditioning didn’t work for 2 days, Couldn’t sleep! They then moved us to another room and gave us champagne and nuts as an apology. We still had to pay for the 2 night os torture."
Laura 6-night trip
Posted less than an hour ago
Hotel Riu Plaza Chicago

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 48 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. Lorado Taft's Midway Studios and Jackson Park Driving Range 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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