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 52 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.

Woodlawn Hotels: 2026 Top 10 Woodlawn Hotels with Limited-Time Deals @Expedia

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

Next weekend

In two weeks

Our top choices for Woodlawn hotels

1. Best Motel By OYO Chicago I-90

Woodlawn

Saul

HK$757 total

includes taxes & fees

4 Oct - 5 Oct

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

Streeterville, 12.6 km from Woodlawn

Shanequa

HK$2,903 total

includes taxes & fees

27 Sept - 28 Sept

3. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 10.4 km from Woodlawn

Pramukha

HK$2,252 total

includes taxes & fees

27 Sept - 28 Sept

4. Crowne Plaza Chicago West Loop by IHG

12.2 km from Woodlawn

Victoria

HK$1,578 total

includes taxes & fees

20 Sept - 21 Sept

5. Hilton Chicago

The Loop, 10.7 km from Woodlawn

Alan

HK$2,204 total

includes taxes & fees

27 Sept - 28 Sept

6. Best Western Grant Park Hotel

The Loop, 10.3 km from Woodlawn

Sara

HK$1,922 total

includes taxes & fees

27 Sept - 28 Sept

7. Hyatt Place Chicago/Downtown - The Loop

The Loop, 12 km from Woodlawn

LISA

HK$2,052 total

includes taxes & fees

27 Sept - 28 Sept

8. Hilton Vacation Club Hotel Blake Chicago

The Loop, 11.1 km from Woodlawn

Ann

HK$2,319 total

includes taxes & fees

14 Oct - 15 Oct

9. Hyatt Regency Chicago

The Loop, 12.3 km from Woodlawn

Whitney

HK$3,395 total

includes taxes & fees

26 Sept - 27 Sept

10. Residence Inn Chicago Downtown/Loop

Theatre District, 11.8 km from Woodlawn

Karla

HK$2,677 total

includes taxes & fees

2 Oct - 3 Oct

11. Swissotel - Chicago

12.2 km from Woodlawn

Aagrim

HK$2,460 total

includes taxes & fees

27 Sept - 28 Sept

12. Sheraton Grand Chicago Riverwalk

Streeterville, 12.4 km from Woodlawn

Brandi

HK$3,255 total

includes taxes & fees

25 Sept - 26 Sept

13. La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 11.9 km from Woodlawn

Mythli

HK$2,099 total

includes taxes & fees

20 Sept - 21 Sept

14. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

12.4 km from Woodlawn

Brock

HK$2,641 total

includes taxes & fees

2 Oct - 3 Oct

15. Hyatt Centric The Loop Chicago

Theatre District, 11.7 km from Woodlawn

Tamika

HK$2,054 total

includes taxes & fees

20 Sept - 21 Sept

16. Fairmont Chicago at Millennium Park

The Loop, 12.1 km from Woodlawn

Amit

HK$2,975 total

includes taxes & fees

20 Sept - 21 Sept

17. Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.6 km from Woodlawn

Brian

HK$1,831 total

includes taxes & fees

27 Sept - 28 Sept

2 restaurants; breakfast, lunch and dinner served

18. LondonHouse Chicago, Curio Collection by Hilton

The Loop, 12.4 km from Woodlawn

Sunny

HK$3,270 total

includes taxes & fees

27 Sept - 28 Sept

19. Congress Plaza Hotel

The Loop, 11 km from Woodlawn

John

HK$1,665 total

includes taxes & fees

7 Oct - 8 Oct

Outdoor pool, pool cabanas (surcharge), pool umbrellas

20. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 12.8 km from Woodlawn

Madelyn

HK$2,009 total

includes taxes & fees

27 Sept - 28 Sept

View all properties

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.

See properties

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.

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 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

Congress Plaza Hotel

10/10 Excellent

"The room was beautiful and immaculate. The location is incredible, so close to everything."

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"liked the location of the hotel, room was nice, the restaurant in the hotel adds to the convenience of the property. I did not like EXPEDIA adding extra charges to my bill tried to get them removed but I couldn't get on web site in order to do it. I did not order the insurance and was charged, next trip I will make sure I don't use Expedias web site."

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

8/10 Good

"There were a couple of things about this hotel that threw me for a loop (no in room coffee machine -- but plenty of coffee at the bar with choice of skim, half and half and cream; you first encounter the bar versus the registration area), but I would definitely stay here again, and for that I compliment the staff. Fatima greeted us at check in and immediately noticed my daughter had mobility issues and offered to change our room for an accessible one. Since this was my first overnight trip with my daughter I hadn't even thought of that! I appreciated that she saw a way to make our stay better and made it happen. Fatima also always had a smile on her face when we saw her and was always ready to answer any question. I didn't get the name of the doorman we interacted with the most (but I did get a photo with him!), which I regret. He was an older many who worked day shift and he touched my heart when he stayed by my daughter while I went to get our car from the parking garage. He didn't have to do that. The people definitely made this staff wonderful!"

Woodlawn hotels in Chicago

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. Homewood Suites by Hilton Chicago Downtown South Loop

4. Crowne Plaza Chicago West Loop by IHG

5. Hilton Chicago

6. Best Western Grant Park Hotel

7. Hyatt Place Chicago/Downtown - The Loop

8. Hilton Vacation Club Hotel Blake Chicago

9. Hyatt Regency Chicago

10. Residence Inn Chicago Downtown/Loop

11. Swissotel - Chicago

12. Sheraton Grand Chicago Riverwalk

13. La Quinta Inn & Suites by Wyndham Chicago Downtown

14. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

15. Hyatt Centric The Loop Chicago

16. Fairmont Chicago at Millennium Park

17. Hilton Chicago/Magnificent Mile Suites

18. LondonHouse Chicago, Curio Collection by Hilton

19. Congress Plaza Hotel

20. DoubleTree by Hilton Chicago - Magnificent Mile

Where to stay in Woodlawn

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Woodlawn Hotel Reviews

Congress Plaza Hotel

Frequently asked questions

Explore a world of travel with Expedia