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 50 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. Obama Presidential Center and 63rd Street Beach are also a couple of places to visit in the neighbourhood. Oak Woods Cemetery, Lorado Taft's Midway Studios and Stony Island Arts Bank 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 Rockefeller Memorial Chapel or Oriental Institute Museum.

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.

The Best Hotels in Woodlawn, Chicago - 2026 Updated Prices

A wooden bridge over a calm river, surrounded by lush greenery and a distant building.

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Our top choices for Woodlawn hotels

1. Best Motel By OYO Chicago I-90

Woodlawn

Roger

฿4,162 total

includes taxes & fees

11 Aug - 12 Aug

2. Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 12.6 km from Woodlawn

Morgan

฿10,615 total

includes taxes & fees

23 Aug - 24 Aug

3. Hyatt Place Chicago/Downtown - The Loop

The Loop, 12 km from Woodlawn

Kimberly

฿9,093 total

includes taxes & fees

23 Aug - 24 Aug

Suite, 1 Bedroom, Corner | Private kitchen | Coffee/tea maker, full-sized fridge, microwave, stovetop

4. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 10.4 km from Woodlawn

jayne

฿7,480 total

includes taxes & fees

19 Aug - 20 Aug

5. Hilton Chicago

The Loop, 10.7 km from Woodlawn

kun

฿13,744 total

includes taxes & fees

6 Aug - 7 Aug

6. Hyatt Regency Chicago

The Loop, 12.3 km from Woodlawn

Emily

฿12,498 total

includes taxes & fees

20 Aug - 21 Aug

7. Hotel Riu Plaza Chicago

Streeterville, 13 km from Woodlawn

Deanne

฿9,550 total

includes taxes & fees

23 Aug - 24 Aug

8. Hilton Garden Inn Chicago Central Loop

The Loop, 11.6 km from Woodlawn

Dawn

฿8,464 total

includes taxes & fees

16 Aug - 17 Aug

9. La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 11.9 km from Woodlawn

Diana

฿7,762 total

includes taxes & fees

9 Aug - 10 Aug

10. Hyatt House Chicago/West Loop-Fulton Market

12.7 km from Woodlawn

Hadi

฿9,814 total

includes taxes & fees

9 Aug - 10 Aug

11. Crowne Plaza Chicago West Loop by IHG

12.2 km from Woodlawn

Navin

฿7,054 total

includes taxes & fees

20 Aug - 21 Aug

12. InterContinental Chicago Magnificent Mile by IHG

Magnificent Mile, 12.7 km from Woodlawn

Jose

฿11,254 total

includes taxes & fees

17 Aug - 18 Aug

13. Aloft by Marriott Chicago Mag Mile

Streeterville, 12.9 km from Woodlawn

Donna

฿7,491 total

includes taxes & fees

9 Aug - 10 Aug

14. Hyatt Place Chicago/River North

River North, 12.8 km from Woodlawn

Michelle

฿6,798 total

includes taxes & fees

23 Aug - 24 Aug

15. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 12.7 km from Woodlawn

Mohana Sandeep

฿8,468 total

includes taxes & fees

10 Aug - 11 Aug

16. Hampton Inn Chicago West Loop Fulton Market Area

12.4 km from Woodlawn

Michele

฿9,214 total

includes taxes & fees

16 Aug - 17 Aug

17. Swissotel - Chicago

12.2 km from Woodlawn

Suzanne

฿10,945 total

includes taxes & fees

16 Aug - 17 Aug

18. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 10.4 km from Woodlawn

Heather

฿7,154 total

includes taxes & fees

9 Aug - 10 Aug

19. Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.6 km from Woodlawn

Jennifer

฿7,395 total

includes taxes & fees

16 Aug - 17 Aug

Premium bedding, in-room safe, desk, blackout curtains

20. Courtyard by Marriott Chicago Magnificent Mile

Streeterville, 12.9 km from Woodlawn

Zachary

฿8,998 total

includes taxes & fees

16 Aug - 17 Aug

View all properties

Where to stay in Woodlawn

Find the best Woodlawn areas for the activities you enjoy most.

A busy city street with tall buildings, a bus, and cars.

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.

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A river with yellow boats, a bridge, and tall buildings.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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A historic castle-like building with intricate stonework and a paved walkway.

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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.

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A river with a city skyline in the background, surrounded by green trees and grass.

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.

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Top Woodlawn Hotel Reviews

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"Great"

Congress Plaza Hotel

8/10 Good

"Staff was helpful especially because I kept locking myself out of my room. It's a bit older hotel so it was a little unclear how to turn off or lower the air because I kept looking for a digital thermostat, buts it's a knob hidden under a little door on the air itself. Bed was comfortable. The room itself has been mostly modernized, but the bath tub was kinda old and had some suspicious brown stains and a bandage shaped thing by the drain that looked painted over. I could not removed either of these with a wet towel. Took a little while for the water to get hot, but when it did, it was hot. There was a lot of street noise from noisy loud motors, sirens, and loud music. My room was connected to another room unfortunately, so I could hear my neighbors's music/TV and every time their FB messenger went off. Wifi didn't really work. Nice location though. Close to public transport and walking distance to the parks and other things I went to."

River Hotel

8/10 Good

"The location was perfect—right next to the Hello Kitty Cafe and the Chicago River, which I absolutely loved! The room was clean and comfortable for my 24-hour stay. I probably should have booked the standard room, but this one still worked out well. The staff was very friendly and helpful throughout my stay. Overall, I had a great experience and would definitely stay here again. Thank you so much!"

Warwick Allerton - Chicago

8/10 Good

"We had a great stay for one night. The location is excellent, right on the main shopping street and within easy walking distance of lots of shops and attractions. The hotel offers reasonably priced luggage storage, which was really convenient, and we were able to check in early for an additional fee, which was worth it after travelling. There’s also a good café in the hotel, perfect for grabbing breakfast or a coffee. The room was a little small and slightly dated, but it was clean, comfortable, and perfectly adequate for what we needed for a one-night stay. Overall, we’d definitely stay here again for the location and convenience."

Search Hotels in Woodlawn, Chicago

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Our top choices for Woodlawn hotels

1. Best Motel By OYO Chicago I-90

2. Sable at Navy Pier Chicago, Curio Collection by Hilton

3. Hyatt Place Chicago/Downtown - The Loop

4. Homewood Suites by Hilton Chicago Downtown South Loop

5. Hilton Chicago

6. Hyatt Regency Chicago

7. Hotel Riu Plaza Chicago

8. Hilton Garden Inn Chicago Central Loop

9. La Quinta Inn & Suites by Wyndham Chicago Downtown

10. Hyatt House Chicago/West Loop-Fulton Market

11. Crowne Plaza Chicago West Loop by IHG

12. InterContinental Chicago Magnificent Mile by IHG

13. Aloft by Marriott Chicago Mag Mile

14. Hyatt Place Chicago/River North

15. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

16. Hampton Inn Chicago West Loop Fulton Market Area

17. Swissotel - Chicago

18. Hilton Garden Inn Chicago Downtown South Loop

19. Hilton Chicago/Magnificent Mile Suites

20. Courtyard by Marriott Chicago Magnificent Mile

Where to stay in Woodlawn

Downtown Chicago

The Loop

Magnificent Mile

River North

Lincoln Park

Top Woodlawn Hotel Reviews

The Allegro Royal Sonesta Hotel Chicago Loop

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