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

₹9,184 total

includes taxes & fees

11 Nov - 12 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

₹19,074 total

includes taxes & fees

22 Nov - 23 Nov

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

3. Hilton Vacation Club Hotel Blake Chicago

The Loop, 11.1 km from Woodlawn

tahira

₹18,127 total

includes taxes & fees

22 Nov - 23 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

JESUS VERA

₹17,151 total

includes taxes & fees

23 Nov - 24 Nov

A cityscape with modern high-rise buildings, a river, and a boat.

5. Hyatt Regency Chicago

The Loop, 12.3 km from Woodlawn

Addison

₹23,183 total

includes taxes & fees

23 Nov - 24 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.

6. L7 Chicago by LOTTE

Theatre District, 12.3 km from Woodlawn

Matthew

₹16,396 total

includes taxes & fees

22 Nov - 23 Nov

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

7. Embassy Suites by Hilton Chicago Downtown River North

River North, 13 km from Woodlawn

Eliana

₹14,322 total

includes taxes & fees

23 Nov - 24 Nov

A multi-story hotel with a modern glass facade, located in an urban setting with a parking lot and street views.

8. Hyatt Place Chicago/River North

River North, 12.8 km from Woodlawn

Pamela

₹13,457 total

includes taxes & fees

22 Nov - 23 Nov

A Fairmont hotel with a prominent entrance, large windows, and a sculpture on the facade.

9. Fairmont Chicago at Millennium Park

The Loop, 12.1 km from Woodlawn

Ruby

₹25,899 total

includes taxes & fees

23 Nov - 24 Nov

A cityscape at dusk with illuminated skyscrapers, a river, and a bridge.

10. Swissotel - Chicago

12.2 km from Woodlawn

Oleg

₹16,543 total

includes taxes & fees

26 Nov - 27 Nov

A hotel room with a large window offering a city view, a bed, a desk, and a chair.

11. Courtyard by Marriott Chicago Magnificent Mile

Streeterville, 12.9 km from Woodlawn

Richard

₹12,960 total

includes taxes & fees

23 Nov - 24 Nov

A cityscape with tall buildings, a river, and a bridge.

12. The Royal Sonesta Chicago Downtown

The Loop, 12.4 km from Woodlawn

Luay

₹17,632 total

includes taxes & fees

26 Nov - 27 Nov

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

13. Eurostars Magnificent Mile

River North, 13.1 km from Woodlawn

Gabriela

₹17,099 total

includes taxes & fees

22 Nov - 23 Nov

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

14. InterContinental Chicago Magnificent Mile by IHG

Magnificent Mile, 12.7 km from Woodlawn

Nellie

₹24,589 total

includes taxes & fees

26 Nov - 27 Nov

A modern building with a colorful facade and a red circular seating area.

15. citizenM Chicago Downtown

Theatre District, 12.3 km from Woodlawn

Katarina

₹13,118 total

includes taxes & fees

23 Nov - 24 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.

16. Aloft by Marriott Chicago Mag Mile

Streeterville, 12.9 km from Woodlawn

Jena

₹12,380 total

includes taxes & fees

22 Nov - 23 Nov

A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

17. Hotel 505 River North

River North, 12.8 km from Woodlawn

Miya

₹15,631 total

includes taxes & fees

22 Nov - 23 Nov

18. Radisson Blu Aqua Hotel Chicago

12.2 km from Woodlawn

Shannon

₹20,754 total

includes taxes & fees

22 Nov - 23 Nov

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

19. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 12.8 km from Woodlawn

Jodi

₹11,438 total

includes taxes & fees

23 Nov - 24 Nov

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

20. Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.6 km from Woodlawn

Melissa

₹13,361 total

includes taxes & fees

23 Nov - 24 Nov

View all properties

Compare popular hotels in Woodlawn

Property	Property class	Guest rating
Best Motel By OYO Chicago I-90	2.5 star property	3.4 157 reviews	View
Sable at Navy Pier Chicago, Curio Collection by Hilton	4.0 star property	9.4 Exceptional 2,763 reviews	View
citizenM Chicago Downtown	4.0 star property	9.4 Exceptional 4,380 reviews	View
Hilton Vacation Club Hotel Blake Chicago	4.0 star property	9.6 Exceptional 1,211 reviews	View
Hilton Garden Inn Chicago Downtown South Loop	3.0 star property	8.8 Excellent 2,205 reviews	View

Where to stay in Woodlawn

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

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

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

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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

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Bbh"

Sports Illustrated Resorts Chicago

8/10 Good

"Solid hotel in a great location. We were there as they were transferring to a full launch of the SI branded hotel. Good gym, rooms are well appointed. During our visit they had an all inclusive rooftop bar from 3-7pm every day which was a great touch but nobody actually told us about it, we kind of found it ourselves. Good option for a hotel in downtown Chicago though!"

Search Hotels in Woodlawn, Chicago

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Our top choices for Woodlawn hotels

1. Best Motel By OYO Chicago I-90

2. LondonHouse Chicago, Curio Collection by Hilton

3. Hilton Vacation Club Hotel Blake Chicago

4. Hotel Riu Plaza Chicago

5. Hyatt Regency Chicago

6. L7 Chicago by LOTTE

7. Embassy Suites by Hilton Chicago Downtown River North

8. Hyatt Place Chicago/River North

9. Fairmont Chicago at Millennium Park

10. Swissotel - Chicago

11. Courtyard by Marriott Chicago Magnificent Mile

12. The Royal Sonesta Chicago Downtown

13. Eurostars Magnificent Mile

14. InterContinental Chicago Magnificent Mile by IHG

15. citizenM Chicago Downtown

16. Aloft by Marriott Chicago Mag Mile

17. Hotel 505 River North

18. Radisson Blu Aqua Hotel Chicago

19. DoubleTree by Hilton Chicago - Magnificent Mile

20. Hilton Chicago/Magnificent Mile Suites

Compare popular hotels in Woodlawn

Where to stay in Woodlawn

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Woodlawn Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

Frequently asked questions

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