Central Chicago Holidays
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Top Flight + Hotel Deals in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was €1,201, price is now €1,023 per person
€1,023
per person
30 Oct - 2 Nov
found 6 hours ago
Return flight included
Shannon (SNN) to Chicago (ORD)
8.2/10 Very Good! (2,096 reviews)
The staff from the start were very nice and helpful. The hotel was clean loved the location of the hotel. Will definitely try booking ag this hotel next year
Reviewed on 2 Sep 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,836, price is now €1,385 per person
€1,385
per person
30 Oct - 2 Nov
found 6 hours ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Our room is perfect to the view that we booked. The room is very spacious and clean.
Reviewed on 2 Sep 2025
Pendry Chicago
Downtown Chicago
Price was €1,385, price is now €1,082 per person
€1,082
per person
30 Oct - 2 Nov
found 6 hours ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
The location was great but overhyped. Rooms were average. I did have good sleep comfy bed and pillows. I would have liked a full length mirror at least. Squeezing a line of people in one elevator and stopping on almost every floor was a little annoying. Wish the front desk explained more of the amenities or a text or something
Reviewed on 2 Sep 2025
Level Chicago – Old Town
Downtown Chicago
Price was €1,302, price is now €1,084 per person
€1,084
per person
30 Oct - 2 Nov
found 6 hours ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
Everything was perfect. Be aware of the expensive it is to park in Chicago.
Reviewed on 2 Sep 2025
Where to stay in Central Chicago
Find the best Central Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Central Chicago
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
Top hotels in Central Chicago
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €198 per night from 15 Sept to 16 Sept
€198
15 Sept - 16 Sept
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €169 per night from 4 Sept to 5 Sept
€169
4 Sept - 5 Sept
includes taxes & fees
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €167 per night from 22 Sept to 23 Sept
€167
22 Sept - 23 Sept
includes taxes & fees
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
Michigan Avenue
4.5/5(14 reviews)
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
4/5(125 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
4.5/5(147 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
What to do in Central 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
96% of travellers recommend
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Flights
Cars
Packages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.