
Central Chicago Cheap Holidays
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Top flight + Cheap hotel deals in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Kimpton Gray Hotel by IHG
Downtown Chicago
Price was £898, price is now £719 per person
£719
per person
20 Jan - 24 Jan
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
I was surprised by the $29.50 daily charge for "Guest Amenity Fee". I did not ask for it. I don't even know what it is. I hate when hotels charge you hidden items.
Reviewed on 9 Nov 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,797, price is now £1,324 per person
£1,324
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Amazing experience! Kurtis and Luis at concierge was great! I had a romantic arrangement in the room before arrival and they made it happen! Great great great 5 ✨
Reviewed on 9 Nov 2026

Pendry Chicago
Downtown Chicago
Price was £1,091, price is now £818 per person
£818
per person
20 Jan - 24 Jan
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on 8 Nov 2026


LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £1,020, price is now £826 per person
£826
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,881 reviews)
Upon arrival we were greeted immediately. The staff helped us unload our bags into a luggage cart and valet took the car to park. Our room was available for early check in. We stayed in the 7th floor in a single king room. Everything was clean and the views were great. We went up to the 22nd floor to see the river views from the rooftop bar. This hotel is in an absolute perfect location to see Chicago. You are close enough to walk to river walk, millennium park, the train, and magnificent mile. We would choose London House again for sure if visiting Chicago.
Reviewed on 9 Nov 2026
Don't see what you're looking for?
See all available trips from London to Central Chicago
View all trips5* Cheap holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,797, price is now £1,324 per person
£1,324
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Amazing experience! Kurtis and Luis at concierge was great! I had a romantic arrangement in the room before arrival and they made it happen! Great great great 5 ✨
Reviewed on 9 Nov 2026

Don't see what you're looking for?
See all available trips from London to Central Chicago
View all trips3 Night Cheap holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Le Méridien Essex Chicago
Downtown Chicago
Price was £984, price is now £854 per person
£854
per person
21 Jan - 24 Jan
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.
Reviewed on 3 Nov 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,272, price is now £1,058 per person
£1,058
per person
21 Jan - 24 Jan
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Amazing experience! Kurtis and Luis at concierge was great! I had a romantic arrangement in the room before arrival and they made it happen! Great great great 5 ✨
Reviewed on 9 Nov 2026

Don't see what you're looking for?
See all available trips from London to Central Chicago
View all trips4 Night Cheap holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.


Pendry Chicago
Downtown Chicago
Price was £1,091, price is now £818 per person
£818
per person
20 Jan - 24 Jan
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on 8 Nov 2026

Don't see what you're looking for?
See all available trips from London to Central Chicago
View all tripsThings to do

Skydeck Chicago at Willis Tower
£32
per adult
84% of travellers recommend

Architecture River Tour from Michigan Avenue
£31
per adult
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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.











