Chicago Holidays from £1,000
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Save up to £335 when you book a flight and hotel together*
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Packages with flights are ATOL protected
Top Chicago Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was £1,715, price is now £1,000 per person
£1,000
per person
16 Oct - 23 Oct
found 19 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,129 reviews)
I would stay at the property again.
Reviewed on 5 Sep 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was £1,803, price is now £1,054 per person
£1,054
per person
6 Nov - 13 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
Beautiful property close to the Fulton Market and night life. The room was eccentric in a way that made our stay cool. It was clean and stocked with a bar & snacks for additional purchase. We enjoyed the Rooftop Cinema on the 6th floor, it was playing my favorite movie! And the restaurant Fora had a delicious breakfast. We definitely recommend this property.
Reviewed on 6 Sep 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,650, price is now £1,572 per person
£1,572
per person
16 Oct - 23 Oct
found 19 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Professional service
Reviewed on 4 Sep 2025
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was £1,811, price is now £1,146 per person
£1,146
per person
16 Oct - 23 Oct
found 19 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (679 reviews)
Room was really clean and amenities were great. Perfect for a small getaway
Reviewed on 6 Sep 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.
Chicago Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 2,720,500 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Chicago Riverwalk, Shedd Aquarium and Art Institute of Chicago |
Top hotels in Chicago
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is £154 per night from 14 Sept to 15 Sept
£154
14 Sept - 15 Sept
includes taxes & fees
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £128 per night from 22 Sept to 23 Sept
£128
22 Sept - 23 Sept
includes taxes & fees
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £145 per night from 22 Sept to 23 Sept
£145
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.
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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. Flight-inclusive packages are ATOL protected.
