Chicago Holidays from £475
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Top Chicago Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was £800, price is now £475 per person
£475
per person
13 Nov - 18 Nov
found 9 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.
Reviewed on 25 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,519, price is now £1,482 per person
£1,482
per person
30 Oct - 6 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on 29 Aug 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was £1,764, price is now £1,055 per person
£1,055
per person
30 Oct - 6 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on 22 Aug 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was £1,374, price is now £867 per person
£867
per person
16 Oct - 21 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on 27 Aug 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
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £131 per night from 4 Sept to 5 Sept
£131
4 Sept - 5 Sept
includes taxes & fees
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £117 per night from 1 Sept to 2 Sept
£117
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (9,045 reviews)
"Very convenient to South Loop sites!"
Reviewed on 26 Aug 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is £146 per night from 3 Sept to 4 Sept
£146
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,802 reviews)
"Very nice,everything is around.Highly recommend."
Reviewed on 27 Aug 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
4.5/5(40 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
What to do in Chicago
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
£33
per adult
96% 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. Flight-inclusive packages are ATOL protected.