Uptown Holidays
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Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
per person
6 Sept - 13 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Wonderful hotel in a great location along the river. The view from Terrace 16 is amazing! Also, the pillows on the bed are really comfortable. I love this hotel and would recommend it to anyone.
Reviewed on 30 Jul 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 13 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (3,357 reviews)
The room was luxurious and pleasant. Location perfect for reaching any activity whether on business or personal visit. Love it!! ❤️💃
Reviewed on 28 Jul 2025
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 13 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).
Reviewed on 27 Jul 2025
Where to stay in Uptown
Find the best Uptown areas and neighborhoods for the activities you enjoy most. Learn more about Uptown
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Top hotels in Uptown
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €180 per night from 4 Aug to 5 Aug
€180
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (9,035 reviews)
"Great value and location. The staff is well train and very friendly"
Reviewed on 29 Jul 2025
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is €260 per night from 17 Aug to 18 Aug
€260
17 Aug - 18 Aug
includes taxes & fees
9/10 Wonderful! (2,124 reviews)
"My two small daughters, 10 and under, and I were on a girls' trip to Chicago and stayed here. They were in awe of how friendly all the guests at the hotel were! Everyone was willing to share a fun fact of the city or just to welcome us. I also appreciated how easy it was to get to places, whether ..."
Reviewed on 29 Jul 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €146 per night from 17 Aug to 18 Aug
€146
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,538 reviews)
"Nice, clean , many things to do around here"
Reviewed on 30 Jul 2025
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
Popular places to visit
Montrose Beach
Soak up the sun with views of Lincoln Park and Lake Michigan at this city beach known for its fun sports and extensive amenities.
Montrose Harbor
With trails, a beach and a bird sanctuary, this spacious city harbor is a good place to sail from and a great place to hang out.
Aragon Ballroom
Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
Things to do
Chicago Sightseeing River and Lake Cruise
€39
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.