
Chicago Holidays
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Top Flight + Hotel Deals in Chicago
Price found within the past 48 hours. Click for updated prices.

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 11 Sept
found 14 hours ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip.
The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.
Reviewed on 21 Jul 2025


LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 11 Sept
found 14 hours 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 - 11 Sept
found 14 hours 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 Chicago
Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago

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 Chicago

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! (9,025 reviews)
"There are areas of the property outside that need some tlc. The hallways are outdated in decor but the room was clean and comfortable. The reception area was very pretty. The staff was courteous and friendly. The hotel itself has a good location walkable to the Soldier Field which we were in town ..."
Reviewed on 29 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is €280 per night from 10 Aug to 11 Aug
€280
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (2,116 reviews)
"Good location where I was able to walk to all the things I wanted to do/see. Convenient to shopping and dining."
Reviewed on 26 Jul 2025

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €144 per night from 17 Aug to 18 Aug
€144
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,542 reviews)
"Excelente hotel Muy buena ubicacion"
Reviewed on 27 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.
Popular places to visit

Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Chicago

Wendella's 90-min Chicago River Architecture Tour
€35
per adult
94% of travellers recommend

Chicago By Night River & Lake Cruise
€39
per adult
94% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.