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 54 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.

Top 10 Woodlawn Hotels of 2026

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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

includes taxes & fees

27 Sept - 28 Sept

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

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

Streeterville, 12.6 km from Woodlawn

Ashraf

includes taxes & fees

30 Aug - 31 Aug

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

3. Congress Plaza Hotel

The Loop, 11 km from Woodlawn

Mia

includes taxes & fees

8 Sept - 9 Sept

A modern interior with a bar area, seating, and decorative wooden panels.

4. Best Western Grant Park Hotel

The Loop, 10.3 km from Woodlawn

Diego

includes taxes & fees

31 Aug - 1 Sept

A large, multi-story hotel with a prominent entrance and classical architectural details.

5. Hilton Chicago

The Loop, 10.7 km from Woodlawn

Konner

includes taxes & fees

9 Sept - 10 Sept

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

6. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 10.4 km from Woodlawn

Dhannetta

includes taxes & fees

7 Sept - 8 Sept

A modern kitchen with a large window, a dining area, and a view of the sea.

7. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 10.4 km from Woodlawn

AMBER

includes taxes & fees

7 Sept - 8 Sept

A spacious lobby with a checkered floor, a large sofa, and multiple chairs.

8. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Streeterville, 12.9 km from Woodlawn

Karaline

includes taxes & fees

7 Sept - 8 Sept

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

9. River Hotel

The Loop, 12.4 km from Woodlawn

Patti

includes taxes & fees

7 Sept - 8 Sept

A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

10. The Wade

Streeterville, 12.9 km from Woodlawn

Ayomikun Jedidiah

includes taxes & fees

30 Aug - 31 Aug

A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

11. Central Loop Hotel

Theatre District, 11.6 km from Woodlawn

Yiyang

includes taxes & fees

30 Aug - 31 Aug

A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

12. Travelodge by Wyndham Downtown Chicago

The Loop, 10.9 km from Woodlawn

Randall

includes taxes & fees

30 Aug - 31 Aug

An outdoor seating area with wicker chairs, a glass-top table, and a sofa with cushions.

13. Hyatt Centric The Loop Chicago

Theatre District, 11.7 km from Woodlawn

Tamika

includes taxes & fees

30 Aug - 31 Aug

A hotel entrance with a glass door, a sign above the door, and two potted plants on either side.

14. Hampton Inn Majestic Chicago Theatre District

Theatre District, 11.7 km from Woodlawn

Richard

includes taxes & fees

8 Sept - 9 Sept

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

15. Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.6 km from Woodlawn

susie

includes taxes & fees

1 Sept - 2 Sept

A multi-story hotel with a prominent 'La Quinta' sign, featuring a modern architectural design with large windows and a flat facade.

16. La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 11.9 km from Woodlawn

Shilpa

includes taxes & fees

30 Aug - 31 Aug

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.

17. Aloft by Marriott Chicago Mag Mile

Streeterville, 12.9 km from Woodlawn

Odessia

includes taxes & fees

7 Sept - 8 Sept

A spacious lobby with a central coffee table, sofas, and a large mirror.

18. The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 14.4 km from Woodlawn

Alma

includes taxes & fees

31 Aug - 1 Sept

A hotel lobby with a bar area, seating, and a large mirror.

19. Hilton Garden Inn Chicago Central Loop

The Loop, 11.6 km from Woodlawn

Theresa

includes taxes & fees

7 Sept - 8 Sept

A hotel with a modern design, featuring a prominent curved glass facade and multiple floors.

20. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 12.7 km from Woodlawn

Rajiv

includes taxes & fees

1 Sept - 2 Sept

View all properties

Where to stay in Woodlawn

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

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.

See properties

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.

See properties

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

Magnificent Mile

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

See properties

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.

See properties

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.

See properties

Top Woodlawn Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Solid"

Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent

"This was one of my favorite stays in Chicago. The rooms are clean, they have a coffee shop and full bar available and the staff was super helpful and friendly. The pool was okay. I would’ve wished for it to be outdoors but my little one loved it no matter what. Breakfast, great. Couldn’t have asked for anything more."

Hotels in Woodlawn

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

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. Congress Plaza Hotel

4. Best Western Grant Park Hotel

5. Hilton Chicago

6. Hilton Garden Inn Chicago Downtown South Loop

7. Homewood Suites by Hilton Chicago Downtown South Loop

8. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

9. River Hotel

10. The Wade

11. Central Loop Hotel

12. Travelodge by Wyndham Downtown Chicago

13. Hyatt Centric The Loop Chicago

14. Hampton Inn Majestic Chicago Theatre District

15. Hilton Chicago/Magnificent Mile Suites

16. La Quinta Inn & Suites by Wyndham Chicago Downtown

17. Aloft by Marriott Chicago Mag Mile

18. The Chicago Hotel Collection Ambassador Gold Coast

19. Hilton Garden Inn Chicago Central Loop

20. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Where to stay in Woodlawn

Downtown Chicago

The Loop

Magnificent Mile

River North

Lincoln Park

Top Woodlawn Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

Frequently asked questions

Explore a world of travel with Expedia