The Best Hotels in Woodlawn, Chicago - 2026 Updated Prices

613-28 Japanese Island Jackson Park Chicago

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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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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.

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Top Woodlawn Hotel Reviews

Marriott Chicago O'Hare

10/10 Excellent

"Rey at the front desk is sooo helpful! Our rental car got delayed due to unexpected issues so we didn’t get to the hotel on Thursday like we supposed to. He took care our check in so efficiently when we got there and understood what we have been through, got our room upgraded and parking. He really made our day a lot better! All the staff we met during our stay were friendly as well. Highly recommend!"

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"PERFECT!!!!! Had such a smooth stay! I had a 5 hour delayed flight and was stuck in Nashville. My bestfriend had already made it to Chicago and was at the hotel. I called the hotel and let them know the situation and they allowed her to check in and get comfortable in our room (which was very beautiful). Breakfast was 10/10, roof top was 10/10, service was 10000/10. Loved everything about the hotel especially since we was walking distance from Michigan Ave. We had such a good time in Chicago and this hotel will forever have a customer anytime I visit. Will be back!"

The Chicago Hotel Collection Ambassador Gold Coast

4/10 Poor

"This review reflects both the hotel and Expedia’s handling of the booking. The good: The location is excellent and very accessible. The common areas, including the lobby and bar, are pleasant and well maintained. The bad: The hotel is showing its age. The AC struggled to keep the room comfortable (both temperature and sound wise), and the carpet and floors felt dirty. Housekeeping did not refill basic toiletries before our stay. The restaurant was disappointing, especially considering the many better dining options nearby. The ugly: Expedia failed to clearly disclose a mandatory “recreation fee” charged by the hotel. In our case, it added $142 to the cost of the stay. After seeing similar complaints in guest reviews, I called Expedia before arrival to clarify. The representative told me that the amount I paid through Expedia should be the only amount due and that I should contact Expedia immediately if the hotel attempted to charge additional mandatory fees. Upon arrival, the hotel presented the extra charge exactly as described by other reviewers. I called Expedia again and, after a lengthy conversation, was told someone would call me back within five minutes and that I would receive a follow-up email. Neither ever happened. Whether the responsibility lies with the hotel or Expedia, the result was the same: unexpected charges, conflicting information, and no follow-through from customer support. Based on this experience, I will not be using Expedia again."

Frequently asked questions

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.

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Our top choices for Woodlawn hotels

Best Motel By OYO Chicago I-90

Sable at Navy Pier Chicago, Curio Collection by Hilton

theWit Chicago, a Hilton Hotel

Omni Chicago Hotel

Hyatt Regency Chicago

Swissotel - Chicago

Congress Plaza Hotel

Eurostars Magnificent Mile

Sheraton Grand Chicago Riverwalk

Hotel Riu Plaza Chicago

Silversmith Hotel Chicago Downtown

LondonHouse Chicago, Curio Collection by Hilton

Palmer House a Hilton Hotel

The Royal Sonesta Chicago Downtown

Radisson Blu Aqua Hotel Chicago

Staypineapple, An Iconic Hotel, The Loop

Fairmont Chicago at Millennium Park

Hilton Garden Inn Chicago Downtown South Loop

Travelodge by Wyndham Downtown Chicago

citizenM Chicago Downtown

Where to stay in Woodlawn

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Woodlawn Hotel Reviews

Marriott Chicago O'Hare

Frequently asked questions

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