Central Chicago Cheap Holidays
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Photo by Phil Ostroff
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- Better togetherSave up to £335 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Top flight + Cheap hotel deals in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was £1,280, price is now £914 per person
£914
per person
24 Apr - 1 May
found 2 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!
Reviewed on 2 Feb 2026
Pendry Chicago
Downtown Chicago
Price was £1,455, price is now £1,009 per person
£1,009
per person
9 Apr - 15 Apr
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on 31 Jan 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,910, price is now £1,389 per person
£1,389
per person
25 Apr - 1 May
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on 3 Feb 2026
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View all trips5* Cheap holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Waldorf Astoria Chicago
Downtown Chicago
Price was £2,841, price is now £2,114 per person
£2,114
per person
14 Mar - 21 Mar
found 2 days ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on 26 Jan 2026
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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.
Arlo Chicago
Downtown Chicago
Price was £841, price is now £705 per person
£705
per person
14 Mar - 17 Mar
found 6 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Room was clean but the soap dispenser at the sync and in shower were not working as it supposed to.
Reviewed on 5 Feb 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was £953, price is now £714 per person
£714
per person
14 Mar - 17 Mar
found 6 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything was amazing, specially the breakfast buffet.
Reviewed on 7 Feb 2026
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View all trips4 Night Cheap holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was £1,135, price is now £923 per person
£923
per person
16 Mar - 20 Mar
found 5 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything was amazing, specially the breakfast buffet.
Reviewed on 7 Feb 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,562, price is now £1,206 per person
£1,206
per person
16 Mar - 20 Mar
found 5 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on 3 Feb 2026
Pendry Chicago
Downtown Chicago
Price was £1,139, price is now £986 per person
£986
per person
16 Mar - 20 Mar
found 5 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on 31 Jan 2026
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See all available trips from Manchester to Central Chicago
View all tripsMore holidays you might like
* 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.
