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 48 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. 63rd Street Beach 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

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Our top choices for Woodlawn hotels

Best Motel By OYO Chicago I-90

Woodlawn

Nyi

includes taxes & fees

13 Feb - 14 Feb

Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 7.8 mi from Woodlawn

Blake

includes taxes & fees

22 Feb - 23 Feb

Palmer House a Hilton Hotel

Theatre District, 7.2 mi from Woodlawn

Melani

includes taxes & fees

21 Feb - 22 Feb

The Wade

Streeterville, 8 mi from Woodlawn

Norah

includes taxes & fees

24 Feb - 25 Feb

Congress Plaza Hotel

The Loop, 6.8 mi from Woodlawn

Jennifer

includes taxes & fees

14 Feb - 15 Feb

Le Méridien Essex Chicago

The Loop, 6.6 mi from Woodlawn

Veronica

includes taxes & fees

5 Mar - 6 Mar

Hotel Riu Plaza Chicago

Streeterville, 8.1 mi from Woodlawn

Brisa

includes taxes & fees

4 Mar - 5 Mar

Swissotel - Chicago

7.6 mi from Woodlawn

Jon

includes taxes & fees

15 Feb - 16 Feb

DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 8 mi from Woodlawn

Robert

includes taxes & fees

18 Feb - 19 Feb

Best Western Grant Park Hotel

The Loop, 6.4 mi from Woodlawn

Doug

includes taxes & fees

23 Feb - 24 Feb

Silversmith Hotel Chicago Downtown

Theatre District, 7.3 mi from Woodlawn

Corey

includes taxes & fees

19 Feb - 20 Feb

Pendry Chicago

Theatre District, 7.6 mi from Woodlawn

Marcelo

includes taxes & fees

15 Mar - 16 Mar

Hilton Chicago

The Loop, 6.7 mi from Woodlawn

Andrea

includes taxes & fees

28 Feb - 1 Mar

Hilton Garden Inn Chicago Downtown South Loop

The Loop, 6.4 mi from Woodlawn

Quayshaun

includes taxes & fees

22 Feb - 23 Feb

Aloft Chicago Mag Mile

Streeterville, 8 mi from Woodlawn

Pablo

includes taxes & fees

24 Feb - 25 Feb

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

The Loop, 6.9 mi from Woodlawn

chris

includes taxes & fees

26 Feb - 27 Feb

Travelodge by Wyndham Downtown Chicago

The Loop, 6.8 mi from Woodlawn

Domenic

includes taxes & fees

18 Feb - 19 Feb

Staypineapple, An Iconic Hotel, The Loop

Theatre District, 7.4 mi from Woodlawn

Lori

includes taxes & fees

26 Feb - 27 Feb

Hyatt Centric The Loop Chicago

Theatre District, 7.3 mi from Woodlawn

Stephanie

includes taxes & fees

27 Feb - 28 Feb

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Theatre District, 7.2 mi from Woodlawn

Kaiya

includes taxes & fees

28 Feb - 1 Mar

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Where to stay in Woodlawn

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

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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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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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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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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O'Hare

Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago.

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