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 47 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.

Top 10 Woodlawn Hotels of 2026

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Our top choices for Woodlawn hotels

Best Motel By OYO Chicago I-90

Woodlawn

Nyi

includes taxes & fees

24 Jan - 25 Jan

River Hotel

The Loop, 12.4 km from Woodlawn

Zach

includes taxes & fees

26 Jan - 27 Jan

Hotel Riu Plaza Chicago

Streeterville, 13 km from Woodlawn

Shyju

includes taxes & fees

4 Feb - 5 Feb

DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 12.8 km from Woodlawn

Jeffrey

includes taxes & fees

1 Feb - 2 Feb

Aloft Chicago Mag Mile

Streeterville, 12.9 km from Woodlawn

Alec

includes taxes & fees

19 Jan - 20 Jan

Claridge House Chicago, Tapestry Collection by Hilton

Gold Coast, 14.4 km from Woodlawn

Anthony

includes taxes & fees

1 Feb - 2 Feb

Warwick Allerton - Chicago

Streeterville, 13.2 km from Woodlawn

Adarsh

includes taxes & fees

27 Jan - 28 Jan

Freehand Chicago

River North, 12.9 km from Woodlawn

Kayla

includes taxes & fees

1 Feb - 2 Feb

Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 12.6 km from Woodlawn

Christine

includes taxes & fees

20 Jan - 21 Jan

Hyatt Regency Chicago

The Loop, 12.3 km from Woodlawn

Donnisha

includes taxes & fees

26 Jan - 27 Jan

Eurostars Magnificent Mile

River North, 13.1 km from Woodlawn

Margie

includes taxes & fees

11 Feb - 12 Feb

Club Quarters Hotel Wacker at Michigan, Chicago

The Loop, 12.4 km from Woodlawn

Kramer

includes taxes & fees

26 Jan - 27 Jan

Rooftop bar, al fresco dining, open daily

The Godfrey Hotel Chicago

River North, 13.3 km from Woodlawn

Alexis

includes taxes & fees

10 Feb - 11 Feb

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 12.7 km from Woodlawn

Jacqueline

includes taxes & fees

21 Jan - 22 Jan

Hilton Garden Inn Chicago Downtown/Magnificent Mile

River North, 12.9 km from Woodlawn

Brandi

includes taxes & fees

20 Jan - 21 Jan

Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.6 km from Woodlawn

Lorenzo Martrel

includes taxes & fees

25 Jan - 26 Jan

Hyatt Centric Chicago Magnificent Mile

Streeterville, 13 km from Woodlawn

Tim

includes taxes & fees

25 Jan - 26 Jan

Congress Plaza Hotel

The Loop, 11 km from Woodlawn

Zach

includes taxes & fees

18 Jan - 19 Jan

La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 11.9 km from Woodlawn

Aimée

includes taxes & fees

30 Jan - 31 Jan

ACME Hotel Chicago, Outset Collection by Hilton

River North, 12.9 km from Woodlawn

Jason

includes taxes & fees

20 Jan - 21 Jan

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Where to stay in Woodlawn

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

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

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

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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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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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