Top Woodlawn Hotels

613-28 Japanese Island Jackson Park Chicago

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Where to stay in Woodlawn

Find the best Woodlawn areas and neighborhoods 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

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

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The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

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River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

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Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

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Top Woodlawn Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"My family and I visited on a very busy weekend. I was displeased initially, that the front desk receptionist was by herself considering the hotel was sold out. However, she handled the check-ins with ease; but because of them being short staffed, the extra towels we needed did not get delivered to the room that night. Other than that the stay was pretty good. They seemed adequately staffed the rest of our stay and we were able to get assisted in a professional, polite manner with the rest of our requests. The property was really nice. I loved the front desk design with old vintage suitcases the most! Great lobby area; cozy, and comfortable. I did not have time to hang out the rooftop but will definitely plan to at my next stay. The location is very walkable and close to all of the great shops on N Michigan. All in all 10/10."

InterContinental Chicago Magnificent Mile by IHG

8/10 Good

"When we arrived our room was dirty. There were used wine glasses, hair beads and rubber bands, and used water bottles. We called and the staff rectified immediately by moving us rooms. Valet was great and so was Micheal Jordan’s Steakhouse. Our bathroom shower had black mold and the vanity was broken and appeared to be glued back together, otherwise nice stay."

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 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 neighborhood that travelers 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 neighborhood.

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 will I be able to find 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 accommodations to choose from.

If I need to cancel my hotel reservation in Woodlawn, will I receive a refund?

Yes! You'll find that most hotel bookings are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of booking. Enter your dates, click on "Search", then use the "fully refundable" filter to view top deals in Woodlawn.

Where can I learn more about changing or cancelling my trip to Woodlawn?

To access more information about updating your trip to Woodlawn or cancelling it, go to https://www.expedia.com/service/.

What can I see and do in this Chicago neighborhood?

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 neighborhood. 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, be sure to visit other sights like 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

The Chicago Hotel Collection - Magnificent Mile

Frequently asked questions

Explore a world of travel with Expedia