Chicago Holidays

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Chicago Holidays

Can't stop daydreaming about Chicago? From flights to room nights, car hire to tours, the committed team at ebookers are the ultimate travel whisperers.

With over 500 partner airlines and more than 500,000 worldwide properties, it's never been easier to escape.

Remember, if you book a Flight + Hotel package with ebookers and see a better deal elsewhere within 48 hours pre check in, we'll match it and repay the difference. That's our Price Guarantee.

Now is the time to start ticking off your lifetime travel dreams. Whether it's a freezing mountain peak or a scorching desert, we'll help you satisfy each and every last wanderlust. Terms and Conditions apply.

More Chicago hotels

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is €150 per night
€150
per night
15 Oct - 16 Oct
0.69 km from city centre
Our customers tell us that they can't get enough of the restaurant at Congress Plaza Hotel. During your stay, you're just a quick walk from Art Institute of Chicago. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
Free WiFi
Restaurant
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
The price is €114 per night
€114
per night
16 Oct - 17 Oct
1.61 km from city centre
Our customers tell us that they can't get enough of the overall value at Warwick Allerton - Chicago. During your stay, you'll be connected to a shopping centre and just a quick walk from Michigan Avenue. Enjoy features like a restaurant, a 24-hour gym and a bar.
Pet-friendly
Restaurant
The Whitehall Hotel

The Whitehall Hotel

4 out of 5
105 E Delaware Pl, Chicago, IL
The price is €130 per night
€130
per night
15 Oct - 16 Oct
2.04 km from city centre
Our customers tell us that they can't get enough of the convenient parking at The Whitehall Hotel. During your stay, you're just a quick walk from Lake Michigan. Free WiFi in public areas, a restaurant and a bar are available.
Pet-friendly
Free WiFi
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
The price is €255 per night
€255
per night
24 Sep - 25 Sep
0.93 km from city centre
Our customers tell us that they can't get enough of the restaurant at Hyatt Regency Chicago. During your stay, you're just a quick walk from Chicago Riverwalk. Enjoy features like free WiFi in public areas, plus 4 restaurants and 2 bars.
Free WiFi
Restaurant
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
The price is €149 per night
€149
per night
24 Sep - 25 Sep
0.81 km from city centre
Our customers tell us that they can't get enough of the overall value at River Hotel. During your stay, you're just a quick walk from Chicago Riverwalk. Features include free WiFi in public areas, plus a restaurant and a gym. This property offers pet-friendly amenities, such as food and water bowls.
Pet-friendly
Free WiFi
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
The price is €241 per night
€241
per night
24 Sep - 25 Sep
0.09 km from city centre
Our customers tell us that they enjoy the overall property condition at Palmer House a Hilton Hotel. During your stay, you're just a quick walk from Millennium Park. Free WiFi in public areas, a full-service spa and an indoor pool are available.
Pool
Spa
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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.

Cheap flights to Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, 28 Oct - Wed, 1 Nov
JFK
New York
ORD
Chicago
€101 Return, found 6 days ago
€101
Return
found 6 days ago
Select Delta flight, departing Sat, 28 Oct from New York to Chicago, returning Wed, 1 Nov, priced at €101 found 6 days ago
Wed, 8 Nov - Tue, 14 Nov
LGA
New York
ORD
Chicago
€101 Return, found 5 days ago
€101
Return
found 5 days ago
Select Delta flight, departing Wed, 8 Nov from New York to Chicago, returning Tue, 14 Nov, priced at €101 found 5 days ago
Sat, 28 Oct - Wed, 1 Nov
EWR
Newark
ORD
Chicago
€150 Return, found 6 days ago
€150
Return
found 6 days ago
Select American Airlines flight, departing Sat, 28 Oct from Newark to Chicago, returning Wed, 1 Nov, priced at €150 found 6 days ago

Chicago neighborhoods

Other holiday destinations

^Savings based on all package bookings with Flight + Hotel made on ebookers.ie from as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.