Woodlawn Holidays
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Price found within the past 48 hours. Click for updated prices.
Hilton Chicago
Downtown Chicago
per person
25 Dec - 30 Dec
found 14 hours ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
8.4/10 Very Good! (1,387 reviews)
it seems like they have Long lines most of the time as I seen that from most of the reviews and when I went, I did experience a long line though I did get there before it filled up too much. I suggest coming in 10 minutes or so before your check in time. our room was nice. We stayed as a couple and we were supposed to get one king bedroom but they cannot accommodate us so they gave us two queen beds, which we were happy with, The room was nice, clean comfortable, although it had a view of the other side of the building so there wasn’t a great view of outside. overall, this place is nice in the architecture in the building is crazy beautiful. they have two or three restaurants I believe and vending machines. parking is easy you can do valet or self Park, self Park also comes with the option to drive in and out.
Reviewed on 15 Nov,2024
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
25 Dec - 30 Dec
found 14 hours ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (263 reviews)
Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!
Reviewed on 11 Nov,2024
The Emily Hotel
Downtown Chicago
per person
25 Dec - 30 Dec
found 14 hours ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (809 reviews)
Lobby and shared space downstairs is beautiful and location is great in Fulton Market. We walked to many bars and restaurants and enjoyed the vibe. The rooms are underwhelming, no closet space, bathroom space lacking, and feel dated despite trying to go for a modern-industrial-chic vibe. The quality of the rooms do not match what the lobby area indicates. The hallways seem like they didn’t get touched in whatever remodel happened here. Overall I think it’s overpriced for what it delivers.
Reviewed on 20 Nov,2024
Arlo Chicago
Downtown Chicago
per person
25 Dec - 30 Dec
found 14 hours ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (1,378 reviews)
Amazing boutique hotel located in downtown Chicago. The front desk staff were so helpful and considerate, as well as the restaurant on property offered multiple options for breakfast lunch dinner and cocktails!
Reviewed on 24 Nov,2024
Where to stay in Woodlawn
Find the best Woodlawn areas and neighborhoods for the activities you enjoy most. Learn more about Woodlawn
Downtown Chicago
5 out of top 10 points of interest in this area
Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
Top hotels in Woodlawn
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$204 per night from 25 Nov to 26 Nov
S$204
includes taxes & fees
25 Nov - 26 Nov
7.8/10 Good! (8,142 reviews)
"Ice machines! This was an issue here all summer long. I pointed it out to management over the summer but the issue has gone from bad to worse. Supposedly, there are ice machines on even floors. This visit, housekeeping directed me to the machine on the 4th floor as the only working ice machine. I ..."
Reviewed on 22 Nov,2024
River Hotel
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$153 per night from 25 Dec to 26 Dec
S$153
includes taxes & fees
25 Dec - 26 Dec
8.6/10 Excellent! (3,551 reviews)
"Is very close to everything"
Reviewed on 23 Nov,2024
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$152 per night from 24 Dec to 25 Dec
S$152
includes taxes & fees
24 Dec - 25 Dec
8.4/10 Very Good! (3,264 reviews)
"This is a go-to hotel for me near a yearly event I participate in. It's the best value of any of the hotels in its immediate surrounding area."
Reviewed on 21 Nov,2024
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.
Frequently asked questions
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
S$58
Per adult
86% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.