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. Lorado Taft's Midway Studios and Jackson Park Driving Range 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

₹9,254 total

includes taxes & fees

24 Jan - 25 Jan

Aloft Chicago Mag Mile

Streeterville, 12.9 km from Woodlawn

Alec

₹8,935 total

includes taxes & fees

1 Feb - 2 Feb

Hotel Riu Plaza Chicago

Streeterville, 13 km from Woodlawn

Freddie

₹14,336 total

includes taxes & fees

3 Feb - 4 Feb

Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.6 km from Woodlawn

Lorenzo Martrel

₹8,650 total

includes taxes & fees

1 Feb - 2 Feb

DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 12.8 km from Woodlawn

Zachary

₹9,181 total

includes taxes & fees

1 Feb - 2 Feb

River Hotel

The Loop, 12.4 km from Woodlawn

Zach

₹8,952 total

includes taxes & fees

24 Jan - 25 Jan

Warwick Allerton - Chicago

Streeterville, 13.2 km from Woodlawn

Adarsh

₹9,829 total

includes taxes & fees

1 Feb - 2 Feb

Congress Plaza Hotel

The Loop, 11 km from Woodlawn

Zyanya

₹14,417 total

includes taxes & fees

14 Feb - 15 Feb

Hyatt Centric The Loop Chicago

Theatre District, 11.7 km from Woodlawn

Luzabeth

₹12,568 total

includes taxes & fees

6 Feb - 7 Feb

Rooftop bar, al fresco dining, open daily

The Godfrey Hotel Chicago

River North, 13.3 km from Woodlawn

Melita Jackson

₹10,573 total

includes taxes & fees

16 Feb - 17 Feb

Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 12.6 km from Woodlawn

Blake

₹14,354 total

includes taxes & fees

2 Feb - 3 Feb

Claridge House Chicago, Tapestry Collection by Hilton

Gold Coast, 14.4 km from Woodlawn

Mary

₹8,783 total

includes taxes & fees

9 Feb - 10 Feb

Silversmith Hotel Chicago Downtown

Theatre District, 11.7 km from Woodlawn

Melissa

Hilton Chicago

The Loop, 10.7 km from Woodlawn

Sabeeh

₹16,727 total

includes taxes & fees

1 Feb - 2 Feb

Hyatt Regency Chicago

The Loop, 12.3 km from Woodlawn

Donnisha

₹19,593 total

includes taxes & fees

8 Feb - 9 Feb

Club Quarters Hotel Wacker at Michigan, Chicago

The Loop, 12.4 km from Woodlawn

Nicholas

₹8,952 total

includes taxes & fees

24 Jan - 25 Jan

Hotel Felix River North/Magnificent Mile

River North, 13.2 km from Woodlawn

Equilla

Freehand Chicago

River North, 12.9 km from Woodlawn

Abby

₹7,428 total

includes taxes & fees

1 Feb - 2 Feb

FOUND Hotel Chicago River North

River North, 13.1 km from Woodlawn

Valerie Louise

₹6,775 total

includes taxes & fees

8 Feb - 9 Feb

Travelodge by Wyndham Downtown Chicago

The Loop, 10.9 km from Woodlawn

Domenic

₹7,869 total

includes taxes & fees

22 Feb - 23 Feb

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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

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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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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