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Woodlawn Hotels, Chicago

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4035 Cheap Hotels in Woodlawn - Specials, Reviews, & Last Minute Deals

Lobby
Silversmith Hotel Chicago Downtown
4.0 star property
9.4 out of 10, Exceptional, (1609)
"It was a perfect no-frills stay in a fantastic location in downtown Chicago. The room was big. There aren’t typical amenities like an ice bucket or even plastic cups for the bathroom, but they did provide two regular bottles of water, so I guess that sufficed. I was able to get a cutlery set from the restaurant when I needed it for my room, so that was good. Check in person, Beverly, was very nice and was so wonderful at giving me an orientation to Chicago. Bed was comfortable. I was here on...
The price is NZ$353
includes taxes & fees
27 May - 28 May
Silversmith Hotel Chicago Downtown
Terrace/patio
citizenM Chicago Downtown
4.0 star property
9.2 out of 10, Wonderful, (1337)
"New hotel in the center of Chicago. High tech youth hostel vibe. Rooms small but very well designed. Perfect for one person but a squeeze for two. Great communal spaces to relax and excellent gym."
The price is NZ$246
includes taxes & fees
27 May - 28 May
citizenM Chicago Downtown
Lobby
LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
9.2 out of 10, Wonderful, (3516)
"The roof top bar-views are second to none. Property is directly on river walk and steps from Michigan Ave and all the shopping one can stand. Hotel is modern and classy!!"
The price is NZ$442
includes taxes & fees
28 May - 29 May
LondonHouse Chicago, Curio Collection by Hilton
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Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.2 out of 10, Wonderful, (1899)
"Great Place for sightseeing! Close to boat tours, carriage tours, right in Navy Pier!"
The price is NZ$413
includes taxes & fees
28 May - 29 May
Sable at Navy Pier Chicago, Curio Collection by Hilton
Rooftop terrace
Virgin Hotels Chicago
4.5 star property
9.2 out of 10, Wonderful, (1015)
"Cool vibe and good value for the rooms. Was a bit loud of an area and windows didn’t have shades to block out sun. Great gym and convenient coffee shop on premises. Would stay again. "
The price is NZ$605
includes taxes & fees
28 May - 29 May
Virgin Hotels Chicago
Terrace/patio
Trump International Hotel & Tower Chicago
5.0 star property
9.2 out of 10, Wonderful, (1190)
"Beautiful experience Top shelf everything This was my 4th stay here while visiting Chicago "
The price is NZ$724
includes taxes & fees
26 May - 27 May
Trump International Hotel & Tower Chicago
Exterior
Loews Chicago Hotel
4.5 star property
9.2 out of 10, Wonderful, (1516)
"Fantastic property!!"
The price is NZ$441
includes taxes & fees
28 May - 29 May
Loews Chicago Hotel
Exterior
Hyatt Regency Chicago
4.0 star property
9.0 out of 10, Wonderful, (3496)
"This big property needs to havw a transport van from airports "
The price is NZ$491
includes taxes & fees
26 May - 27 May
Hyatt Regency Chicago
Exterior
The Royal Sonesta Chicago Downtown
4.0 star property
9.0 out of 10, Wonderful, (1933)
"Very clean and well maintained. It’s in a very busy location but convenient to walk around. "
The price is NZ$456
includes taxes & fees
28 May - 29 May
The Royal Sonesta Chicago Downtown
Cocktail bar
ACME Hotel Company
3.5 star property
9.0 out of 10, Wonderful, (1397)
"I enjoyed my hassle-free stay! "
The price is NZ$246
includes taxes & fees
28 May - 29 May
ACME Hotel Company
Exterior
Hyatt Place Chicago/River North
3.5 star property
9.0 out of 10, Wonderful, (1395)
"It was amazing. "
The price is NZ$319
includes taxes & fees
28 May - 29 May
Hyatt Place Chicago/River North
Exterior
InterContinental Chicago Magnificent Mile, an IHG Hotel
4.5 star property
8.8 out of 10, Excellent, (1583)
"I"
The price is NZ$432
includes taxes & fees
27 May - 28 May
InterContinental Chicago Magnificent Mile, an IHG Hotel
City view from property
voco Chicago Downtown, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (1187)
"Jasmine was amazing! She always made sure my guest and I were doing well and she was helping to help us even when she wasn’t clocked in!"
The price is NZ$351
includes taxes & fees
28 May - 29 May
voco Chicago Downtown, an IHG Hotel
Aerial view
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (1018)
"It was Amazing problem when it was time to check in and out two charges were put on our cards it Supposed been splits between 3 people charge each individual card "
The price is NZ$332
includes taxes & fees
28 May - 29 May
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Lobby
Hyatt Centric Chicago Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (1300)
"The hotel was fine. It is extremely central to most usual tourist activities and worked really well in that regard. It has a weird entryway that you enter on the ground floor that is not the hotel and you go up a floor or so and then enter the hotel lobby. They have disposable plastic cups further wrapped in plastic instead of real drinking glasses. This was unusual and felt cheap. They have paper cups instead of real coffee cups which is less uncommon. Both of these felt eco unfriendly....
The price is NZ$426
includes taxes & fees
27 May - 28 May
Hyatt Centric Chicago Magnificent Mile
Daily cooked-to-order breakfast for a fee
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2206)
"Staying at the Aloft is very central and walkable to most things. With concrete walls the rooms are quite as we didnt hear anything from next door. Close to shopping and dining options. Walkable to Mag mile and Navy Pier. We caught the train from the airport with a short walk to the hotel without changes from train to bus."
The price is NZ$369
includes taxes & fees
27 May - 28 May
Aloft Chicago Mag Mile
Exterior
Club Quarters Hotel, Central Loop, Chicago
4.0 star property
8.6 out of 10, Excellent, (3057)
"Love this property and location! "
The price is NZ$280
includes taxes & fees
28 May - 29 May
Club Quarters Hotel, Central Loop, Chicago
Front of property - evening/night
Fairmont Chicago at Millennium Park
4.5 star property
8.6 out of 10, Excellent, (1486)
"Requested a fridge and microwave, as they do not come in each room. Wasn't there when we checked in, but came shortly and worked well. Nice hotel, but no pool and they only offer parking as a valet service for $80+ per day. Ended up parking at Aon Center for $17/day, which was VERY close. "
The price is NZ$430
includes taxes & fees
28 May - 29 May
Fairmont Chicago at Millennium Park
Rooftop bar, al fresco dining, open daily
The Godfrey Hotel Chicago
4.5 star property
8.6 out of 10, Excellent, (1544)
"Staff is absolutely wonderful & genuinely helpful!"
The price is NZ$427
includes taxes & fees
23 May - 24 May
The Godfrey Hotel Chicago
Terrace/patio
Home2 Suites by Hilton Chicago River North
3.0 star property
8.4 out of 10, Very good, (1487)
"Nice rooms"
The price is NZ$313
includes taxes & fees
27 May - 28 May
Home2 Suites by Hilton Chicago River North
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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.

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 27 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?

Ready to get out and explore the city? Cottage Grove Station is the closest metro station. To venture out of town, take a train from Chicago 63rd Street Station.