Woodlawn Hotels: 2026 Top 10 Woodlawn Hotels with Limited-Time Deals @Expedia

A wooden bridge over a calm river, surrounded by lush greenery and a distant building.

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Where to stay in Woodlawn

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

A busy city street with tall buildings, a bus, and cars.

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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A historic castle-like building with intricate stonework and a paved walkway.

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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A river with yellow boats, a bridge, and tall buildings.

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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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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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A river with a city skyline in the background, surrounded by green trees and grass.

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

The Wade

8/10 Good

"Why book here? LOCATION and competitive price. Why not? If you care about hospitality. This isn't going to be the place. Some of the front desk staff were impatient and border line dismissive. No decaf, despite a sign saying it was available. Just plan to go to Starbucks about a block away for coffee of any quality. Check in evening staff, told us breakfast would be served (Marriott member) and then we weren't given the magic card. Morning staff said we didn't qualify and we got the signal NOT to bother them with unreasonable questions. Our room was next to elevator and I was glad I had my ear plugs. No coffee in rooms. Weird kinda sensual picture of red lips predominant art in room... not family friendly or sensitive to women's modern issues. Views of lake were great! Easy walking location to see Lake Shore Drive and Many other great attractions. LOVED the beach and lake. It is amazingly clear water. Just have realistic expectations that this is a place to sleep and the staff may not care or are burned out. Great service oriented humans are expensive. You're not paying for that here."

Congress Plaza Hotel

8/10 Good

"Room was pretty neat. Had a vibe to it. Almost a haunted 1930s vibe in the room I stayed in. Only complaint was the air conditioning. Couldn't keep up on the 11th floor. Throughout the night it caught up. Bathroom was nice, very clean. Pool would of been nice. Within walking distance to the main attractions. Da Bears, Field Museum, Planterium, Aquarium, Cloud whatever(the bean), and the Love and Marriage fountain."

The Royal Sonesta Chicago Downtown

8/10 Good

"One main concern with the room is the rainfall shower head. It’s not conducive to Black hair as we don't fully immerse out head in water during showers. Even pushing the head towards the wall offered minimal help. Breakfast at Hoyt is expensive and there isnt much variety on the menu. The location of the hotel is perfectly near the Riverwalk. Microwaves are available upon request. Early checkin is an option at a cost unless u are a rewards member. There is no pool plus a $30 a day non refundable resort fee AND a $100 a day deposit. My opinion, not much bang for your buck. The hotel was emailed 2 weeks prior to my arrival in order to plan something special however the email was never answered."

Hyatt Regency Chicago

10/10 Excellent

"I had a wonderful stay. The location was perfect—right along the river and within walking distance of many of Chicago’s top attractions, restaurants, and shopping. The hotel was clean, modern, and well-maintained. My room was spacious, comfortable, and offered beautiful views of the city. The staff was friendly, professional, and always willing to help. The standard check-in is at 3 pm but when I arrived at 11 am the staff was able to give me a room upon my arrival. My entire stay smooth and enjoyable."

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 49 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. Obama Presidential Center and 63rd Street Beach are also a couple of places to visit in the neighbourhood. Oak Woods Cemetery, Lorado Taft's Midway Studios and Stony Island Arts Bank 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 Rockefeller Memorial Chapel or Oriental Institute Museum.

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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Woodlawn hotels in Chicago

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Our top choices for Woodlawn hotels

1. Best Motel By OYO Chicago I-90

2. Sable at Navy Pier Chicago, Curio Collection by Hilton

3. Homewood Suites by Hilton Chicago Downtown South Loop

4. Hilton Chicago

5. Hilton Garden Inn Chicago Central Loop

6. Hyatt Place Chicago/Downtown - The Loop

7. Hyatt House Chicago/West Loop-Fulton Market

8. Hyatt Regency Chicago

9. La Quinta Inn & Suites by Wyndham Chicago Downtown

10. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

11. Best Western Grant Park Hotel

12. Hotel Riu Plaza Chicago

13. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

14. Hampton Inn Chicago West Loop Fulton Market Area

15. Hilton Garden Inn Chicago Downtown South Loop

16. Hyatt Place Chicago/River North

17. Swissotel - Chicago

18. Crowne Plaza Chicago West Loop by IHG

19. LondonHouse Chicago, Curio Collection by Hilton

20. Hyatt Centric The Loop Chicago

Where to stay in Woodlawn

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Woodlawn Hotel Reviews

The Wade

Frequently asked questions

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