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.
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,483, price is now £999 per person
£999
per person
10 Nov - 14 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £2,303, price is now £1,465 per person
£1,465
per person
8 Oct - 15 Oct
found 21 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Loved the view from the room of Lake Michigan.
Reviewed on 25 Aug 2025
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was £2,172, price is now £1,399 per person
£1,399
per person
8 Oct - 15 Oct
found 21 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.
Reviewed on 25 Aug 2025
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was £2,020, price is now £1,307 per person
£1,307
per person
8 Oct - 15 Oct
found 21 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Great property. Clean and convenient. Only unsightly thing is that there was a dirty t shirt laying in the hallway that nobody seemed to pick up.
Reviewed on 26 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,554, price is now £1,014 per person
£1,014
per person
27 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.
Reviewed on 25 Aug 2025
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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.
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,483, price is now £999 per person
£999
per person
10 Nov - 14 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,554, price is now £1,014 per person
£1,014
per person
27 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.
Reviewed on 25 Aug 2025
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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,296, price is now £995 per person
£995
per person
8 Nov - 11 Nov
found 22 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.
Reviewed on 25 Aug 2025
The Royal Sonesta Chicago River North
Downtown Chicago
Price was £1,874, price is now £1,431 per person
£1,431
per person
10 Oct - 13 Oct
found 14 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Great location and room was fantastic! Only negatives were a lengthy check in and access to the outside deck was closed at 10 PM. Probably a good idea for that, but it would’ve been nice to go out there for a nightcap.
Reviewed on 26 Aug 2025
Fairmont Chicago at Millennium Park Gold Experience
Downtown Chicago
Price was £1,814, price is now £1,420 per person
£1,420
per person
10 Oct - 13 Oct
found 14 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (131 reviews)
You can walk to restaurants and Michigan ave and the area is nice and safe
Reviewed on 16 Jul 2025
Don't see what you're looking for?
See all available trips from Manchester to Central Chicago
View all trips4 Night Cheap holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
Downtown Chicago
Price was £1,224, price is now £829 per person
£829
per person
27 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,182 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
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,554, price is now £1,014 per person
£1,014
per person
27 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.
Reviewed on 25 Aug 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,631, price is now £1,087 per person
£1,087
per person
29 Sept - 3 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug 2025
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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.