Photo by Tanesha Thompson
Hotels in Woodlawn
Free cancellation options if plans change
Earn rewards on every night you stay
Save more with Member Prices
Check prices for these dates
Where to stay in Woodlawn?
3.4 out of 10, (48)
3.4/10
(48)
The price is HK$436
HK$436
HK$566 total
includes taxes & fees
14 Jan - 15 Jan 2026
8.0 out of 10, Very good, (2652)
8.0/10
Very good
(2652)
The price is HK$455
HK$455
HK$671 total
includes taxes & fees
4 Jan - 5 Jan 2026
Club Quarters Hotel Wacker at Michigan, Chicago
Club Quarters Hotel Wacker at Michigan, Chicago4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (1991)
8.8/10
Excellent
(1991)
The price is HK$647
HK$647
HK$760 total
includes taxes & fees
21 Dec - 22 Dec
8.6 out of 10, Excellent, (2964)
8.6/10
Excellent
(2964)
The price is HK$628
HK$628
HK$738 total
includes taxes & fees
4 Jan - 5 Jan 2026
8.0 out of 10, Very good, (9668)
8.0/10
Very good
(9668)
The price is HK$1,604
HK$1,604
HK$1,883 total
includes taxes & fees
31 Dec - 1 Jan 2026
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago4.0 star property
Theatre District, 11.6 km from Woodlawn
8.8 out of 10, Excellent, (3316)
8.8/10
Excellent
(3316)
The price is HK$647
HK$647
HK$760 total
includes taxes & fees
21 Dec - 22 Dec
8.4 out of 10, Very good, (2395)
8.4/10
Very good
(2395)
The price is HK$887
HK$887
HK$1,269 total
includes taxes & fees
26 Dec - 27 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by Hilton4.0 star property
Streeterville, 12.6 km from Woodlawn
9.4 out of 10, Exceptional, (2271)
9.4/10
Exceptional
(2271)
The price is HK$659
HK$659
HK$1,038 total
includes taxes & fees
20 Jan - 21 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent Mile4.0 star property
Streeterville, 12.7 km from Woodlawn
8.4 out of 10, Very good, (2747)
8.4/10
Very good
(2747)
The price is HK$644
HK$644
HK$984 total
includes taxes & fees
11 Jan - 12 Jan 2026
Warwick Allerton - Chicago
Warwick Allerton - Chicago4.0 star property
Magnificent Mile, 13.1 km from Woodlawn
8.4 out of 10, Very good, (3009)
8.4/10
Very good
(3009)
The price is HK$519
HK$519
HK$838 total
includes taxes & fees
15 Jan - 16 Jan 2026
Best Western Grant Park Hotel
Best Western Grant Park Hotel2.5 star property
The Loop, 10.4 km from Woodlawn
8.2 out of 10, Very good, (2651)
8.2/10
Very good
(2651)
The price is HK$560
HK$560
HK$658 total
includes taxes & fees
6 Jan - 7 Jan 2026
9.4 out of 10, Exceptional, (3403)
9.4/10
Exceptional
(3403)
The price is HK$1,082
HK$1,082
HK$1,498 total
includes taxes & fees
5 Jan - 6 Jan 2026
8.8 out of 10, Excellent, (4852)
8.8/10
Excellent
(4852)
The price is HK$647
HK$647
HK$760 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent Mile3.0 star property
River North, 12.8 km from Woodlawn
8.4 out of 10, Very good, (4264)
8.4/10
Very good
(4264)
The price is HK$638
HK$638
HK$749 total
includes taxes & fees
11 Jan - 12 Jan 2026
Hyatt Centric Chicago Magnificent Mile
Hyatt Centric Chicago Magnificent Mile4.0 star property
Streeterville, 13 km from Woodlawn
9.0 out of 10, Wonderful, (1054)
9.0/10
Wonderful
(1054)
The price is HK$763
HK$763
HK$1,124 total
includes taxes & fees
6 Jan - 7 Jan 2026
8.6 out of 10, Excellent, (1943)
8.6/10
Excellent
(1943)
The price is HK$634
HK$634
HK$745 total
includes taxes & fees
2 Jan - 3 Jan 2026
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel4.0 star property
Theatre District, 11.7 km from Woodlawn
8.4 out of 10, Very good, (2153)
8.4/10
Very good
(2153)
The price is HK$989
HK$989
HK$1,355 total
includes taxes & fees
26 Dec - 27 Dec
9.4 out of 10, Exceptional, (3013)
9.4/10
Exceptional
(3013)
The price is HK$705
HK$705
HK$1,046 total
includes taxes & fees
6 Jan - 7 Jan 2026
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago2.0 star property
The Loop, 10.9 km from Woodlawn
7.4 out of 10, Good, (2497)
7.4/10
Good
(2497)
The price is HK$608
HK$608
HK$714 total
includes taxes & fees
19 Jan - 20 Jan 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
When is the best time to visit Chicago?
When is the best time to visit Chicago?Our prices for hotels in Chicago are cheapest in April
When is the best time to visit Chicago?
When is the best time to visit Chicago?
Our prices for hotels in Chicago are cheapest in April
Price trends for hotels in Chicago
Pricing is based on two traveller single night rates
Currently viewing crowd sizes and weather for December.
Typical weather for Chicago
December
High crowds
High 3°C / low -2°C. Cloudy most days.
View properties in December 3°
December, High crowds, average high temperature 3 degrees Celsius, average low temperature -2 degrees Celsius. Cloudy most days.
-2°
-1°
January, Low crowds, average high temperature -1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
0°
February, Low crowds, average high temperature 0 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
6°
March, Low crowds, average high temperature 6 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
0°
11°
April, Low crowds, average high temperature 11 degrees Celsius, average low temperature 5 degrees Celsius. Partly sunny.
5°
17°
May, Moderate crowds, average high temperature 17 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
11°
23°
June, High crowds, average high temperature 23 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
26°
July, High crowds, average high temperature 26 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
20°
26°
August, High crowds, average high temperature 26 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
20°
23°
September, Moderate crowds, average high temperature 23 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
16°
October, Moderate crowds, average high temperature 16 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
10°
8°
November, Moderate crowds, average high temperature 8 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
3°
Monthly weather averages (˚C)
Top landmarks in Woodlawn
Bob-O-Link Meadow
Woodlawn is home to Bob-O-Link Meadow, so why not stop by during your stay in Chicago? Let yourself be amazed at the art galleries and museums in the area too. If you have fun at Bob-O-Link Meadow, you'll love Griffin Museum of Science and Industry and Garden of the Phoenix, both a short walk away.
Check out reviews of Woodlawn hotels guests love
The Whitehall Hotel, BW Premier Collection
10/10 Excellent
"Great location, very clean room!"
Embassy Suites by Hilton Chicago Downtown River North
10/10 Excellent
"The inside Italian restaurant was fabulous."
Pendry Chicago
10/10 Excellent
"Excellent location to stay in the heart of the city. "
Sable at Navy Pier Chicago, Curio Collection by Hilton
10/10 Excellent
"Friendly staff, beautiful and clean rooms. "
Club Quarters Hotel Wacker at Michigan, Chicago
10/10 Excellent
"Great friendy staff, Smooth Check-in Check-out Process and the view from the room was just stunning. "
Eurostars Magnificent Mile
10/10 Excellent
"Clean room"
Crowne Plaza Chicago West Loop by IHG
10/10 Excellent
"Location and friendly staff "
InterContinental Chicago Magnificent Mile by IHG
10/10 Excellent
"Outstanding location and services. "
Silversmith Hotel Chicago Downtown
10/10 Excellent
"The rooms were comfortable and spacious. The bed was comfortable. The vent up near the ceiling in my room needed to be cleaned. The shower was fantastic. Could have used instructions on how to use the coffee maker lol. The location was amazing! We hung out down in the lobby area and the staff were super nice. We had some shareables to eat and everything was good. We did not eat breakfast. I would recommend and stay here again. "
Frequently asked questions
Is Woodlawn expensive to stay in?
You can find great hotels from HK$566 in Woodlawn to suit a range of budgets. To find the best low-cost hotel on Hotels.com that meets your needs, apply your search filters and then sort hotels by "Price: low to high".
How can I find discounted rates and deals for Woodlawn hotels?
Discover great deals on hotels in Woodlawn with Hotels.com. Sign up for free to unlock member only prices and start earning rewards. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Woodlawn hotels.
How can I find discounted rates and deals for Woodlawn hotels?
Unlocking discounted rates at hotels in Woodlawn couldn't be simpler. Members save up to 20% on select hotels when signed in. Silver, Gold, and Platinum members can earn additional rewards on VIP Access bookings.
Can I receive a refund if I cancel my Woodlawn hotel booking?
The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel your booking. Some Woodlawn hotels require you to cancel more than 24 hours before check-in, so look at your booking beforehand. For extra peace of mind before you book, filter hotels by "Property cancellation options" and select "Fully refundable property".
Is it worth staying in Woodlawn?
You're spoilt for choice with 46 hotels in the area so it's easy to find your perfect somewhere. Basing yourself in Woodlawn makes it easy to explore Chicago, including the areas of Near South Side and Hyde Park.
Find out more about Woodlawn