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 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.

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

A room with large windows, a wooden floor, and a built-in air conditioning unit.

1. Best Motel By OYO Chicago I-90

Woodlawn

Saul

Rp1.740.507 total

includes taxes & fees

1 Nov - 2 Nov

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

2. LondonHouse Chicago, Curio Collection by Hilton

The Loop, 12.4 km from Woodlawn

James

Rp5.290.880 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.

3. Hilton Vacation Club Hotel Blake Chicago

The Loop, 11.1 km from Woodlawn

Mario

Rp3.683.096 total

includes taxes & fees

3 Nov - 4 Nov

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

4. Hotel Riu Plaza Chicago

Streeterville, 13 km from Woodlawn

Scott E

Rp4.481.000 total

includes taxes & fees

11 Nov - 12 Nov

A room with two chairs and a small table, a large window with a city view at night.

5. Eurostars Magnificent Mile

River North, 13.1 km from Woodlawn

Will

Rp3.257.708 total

includes taxes & fees

1 Nov - 2 Nov

The Intercontinental hotel facade with a large American flag and a floral display.

6. InterContinental Chicago Magnificent Mile by IHG

Magnificent Mile, 12.7 km from Woodlawn

Said Lopez

Rp5.174.592 total

includes taxes & fees

31 Oct - 1 Nov

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

7. L7 Chicago by LOTTE

Theatre District, 12.3 km from Woodlawn

Jeffrey Thomas

Rp3.558.835 total

includes taxes & fees

1 Nov - 2 Nov

A spacious bar area with high ceilings and large windows, offering views of a cityscape.

8. Hyatt Regency Chicago

The Loop, 12.3 km from Woodlawn

Addison

Rp5.743.910 total

includes taxes & fees

31 Oct - 1 Nov

A modern restaurant interior with a green wall, hanging lights, and a long dining area.

9. Hotel 505 River North

River North, 12.8 km from Woodlawn

Jordan

Rp4.413.473 total

includes taxes & fees

15 Nov - 16 Nov

A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

10. Hyatt Place Chicago/River North

River North, 12.8 km from Woodlawn

Nilofar

Rp3.729.221 total

includes taxes & fees

12 Nov - 13 Nov

A dining area with a table set for four, large windows offering a cityscape view at dusk.

11. The Royal Sonesta Chicago Downtown

The Loop, 12.4 km from Woodlawn

Jordyn

Rp4.198.922 total

includes taxes & fees

1 Nov - 2 Nov

A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

12. Embassy Suites by Hilton Chicago Downtown River North

River North, 13 km from Woodlawn

Eliana

Rp3.260.924 total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with a marble island, fruit bowls, and a city view.

13. Fairmont Chicago at Millennium Park

The Loop, 12.1 km from Woodlawn

Ruby

Rp7.051.622 total

includes taxes & fees

25 Oct - 26 Oct

A dining table set for six with a cityscape view through large windows.

14. Swissotel - Chicago

12.2 km from Woodlawn

Hilary

Rp5.437.891 total

includes taxes & fees

9 Nov - 10 Nov

A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

15. Aloft by Marriott Chicago Mag Mile

Streeterville, 12.9 km from Woodlawn

Jonathan M

Rp3.101.038 total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

16. Silversmith Hotel Chicago Downtown

Theatre District, 11.7 km from Woodlawn

Guy

Rp3.648.971 total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

17. Palmer House a Hilton Hotel

Theatre District, 11.7 km from Woodlawn

Christy

Rp4.616.652 total

includes taxes & fees

31 Oct - 1 Nov

A modern rooftop lounge with white seating, a glass ceiling, and city views.

18. The Godfrey Hotel Chicago

River North, 13.3 km from Woodlawn

Hector

Rp3.253.124 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor seating area with modern furniture and potted plants.

19. Radisson Blu Aqua Hotel Chicago

12.2 km from Woodlawn

Shannon

Rp5.630.669 total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

20. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 10.4 km from Woodlawn

Aran

Rp3.169.835 total

includes taxes & fees

12 Nov - 13 Nov

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Where to stay in Woodlawn

Find the best Woodlawn areas for the activities you enjoy most. Learn more about Woodlawn

A cityscape with tall skyscrapers and a historic tower.

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 busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

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 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 large, historic building with a central tower and multiple windows, located near a body of water.

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

River Hotel

8/10 Good

"The room had a great view of the river, but there was 2 things that didn’t work for me, the first one the AC unit, the first day that we arrived it was hot, we turned on the AC unit and it didn’t cool enough the room, so that night we had a hard time trying to sleep, the day after I report the issue and they fix it, the second one was the tv, half screen had a blue stain like the tv was damaged"