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 49 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

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Our top choices for Woodlawn hotels

1. Best Motel By OYO Chicago I-90

Woodlawn

Roger

RM395 total

includes taxes & fees

25 Aug - 26 Aug

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

Streeterville, 12.6 km from Woodlawn

Dawn

RM1,014 total

includes taxes & fees

7 Sept - 8 Sept

3. Hilton Chicago

The Loop, 10.7 km from Woodlawn

kun

RM943 total

includes taxes & fees

7 Sept - 8 Sept

4. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 10.4 km from Woodlawn

jayne

RM761 total

includes taxes & fees

7 Sept - 8 Sept

Outdoor pool, pool cabanas (surcharge), pool umbrellas

5. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 12.8 km from Woodlawn

Macy

RM781 total

includes taxes & fees

30 Aug - 31 Aug

6. Aloft by Marriott Chicago Mag Mile

Streeterville, 12.9 km from Woodlawn

Jasmin

RM768 total

includes taxes & fees

16 Aug - 17 Aug

7. Best Western Grant Park Hotel

The Loop, 10.3 km from Woodlawn

Melissa

RM696 total

includes taxes & fees

30 Aug - 31 Aug

8. Hilton Garden Inn Chicago Central Loop

The Loop, 11.6 km from Woodlawn

Dawn

RM806 total

includes taxes & fees

7 Sept - 8 Sept

9. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

The Loop, 11.1 km from Woodlawn

Melanie

RM813 total

includes taxes & fees

7 Sept - 8 Sept

10. Hotel Riu Plaza Chicago

Streeterville, 13 km from Woodlawn

Cicely

RM1,036 total

includes taxes & fees

31 Aug - 1 Sept

11. Crowne Plaza Chicago West Loop by IHG

12.2 km from Woodlawn

Evelyn

RM757 total

includes taxes & fees

30 Aug - 31 Aug

12. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 12.7 km from Woodlawn

JENNIFER

RM1,009 total

includes taxes & fees

1 Sept - 2 Sept

13. Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.6 km from Woodlawn

Jennifer

RM781 total

includes taxes & fees

30 Aug - 31 Aug

14. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Streeterville, 12.9 km from Woodlawn

Jeffrey

RM699 total

includes taxes & fees

30 Aug - 31 Aug

15. Hyatt Place Chicago/Downtown - The Loop

The Loop, 12 km from Woodlawn

Kimberly

RM773 total

includes taxes & fees

7 Sept - 8 Sept

2 restaurants; breakfast, lunch and dinner served

16. LondonHouse Chicago, Curio Collection by Hilton

The Loop, 12.4 km from Woodlawn

Luis

RM1,150 total

includes taxes & fees

7 Sept - 8 Sept

17. Silversmith Hotel Chicago Downtown

Theatre District, 11.7 km from Woodlawn

Gillian

RM903 total

includes taxes & fees

30 Aug - 31 Aug

18. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 10.4 km from Woodlawn

Jordan Leigh

RM781 total

includes taxes & fees

30 Aug - 31 Aug

19. Hyatt Regency Chicago

The Loop, 12.3 km from Woodlawn

Emily

RM1,260 total

includes taxes & fees

30 Aug - 31 Aug

20. La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 11.9 km from Woodlawn

Paige

RM769 total

includes taxes & fees

8 Sept - 9 Sept

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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

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 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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The Chicago Theatre with illuminated marquee and a wet street reflecting lights.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

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