Central Chicago Cheap Holidays
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- 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.
Le Méridien Essex Chicago
Downtown Chicago
Price was £1,690, price is now £1,270 per person
£1,270
per person
29 Aug - 5 Sept
found 11 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.8/10 Excellent! (1,013 reviews)
Very clean and great view to the park. Staffs are helpful and respectful.
Reviewed on 20 Jun 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,854, price is now £2,098 per person
£2,098
per person
27 Aug - 3 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
It was everything I expected! The staff was amazing. Everything ran smoothly. I would say the pool could use a little updating. Everything was delightful. Definitely will be back.
Reviewed on 24 Jun 2026
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
Price was £3,210, price is now £2,382 per person
£2,382
per person
29 Aug - 5 Sept
found 11 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
We love the Peninsula! The staff, location, room, and the Shanghai restaurant top tier.
Reviewed on 21 Jun 2026
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was £3,341, price is now £2,483 per person
£2,483
per person
29 Aug - 5 Sept
found 11 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.8/10 Exceptional! (1,011 reviews)
The spa was a terrific experience.
Reviewed on 22 Jun 2026
Kinzie Hotel
Downtown Chicago
Price was £1,675, price is now £1,278 per person
£1,278
per person
7 Sept - 14 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (2,146 reviews)
We enjoyed our stay at the Kinzie Hotel. A good location and helpful staff made for a nice visit!
Reviewed on 24 Jun 2026
Don't see what you're looking for?
See all available trips from Manchester 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
Save 100% on your flight
Price was £2,854, price is now £2,098 per person
£2,098
per person
27 Aug - 3 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
It was everything I expected! The staff was amazing. Everything ran smoothly. I would say the pool could use a little updating. Everything was delightful. Definitely will be back.
Reviewed on 24 Jun 2026
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
Price was £3,210, price is now £2,382 per person
£2,382
per person
29 Aug - 5 Sept
found 11 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
We love the Peninsula! The staff, location, room, and the Shanghai restaurant top tier.
Reviewed on 21 Jun 2026
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was £3,341, price is now £2,483 per person
£2,483
per person
29 Aug - 5 Sept
found 11 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.8/10 Exceptional! (1,011 reviews)
The spa was a terrific experience.
Reviewed on 22 Jun 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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was £862, price is now £691 per person
£691
per person
2 Sept - 5 Sept
found 2 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Terrible attitude of the front desk clerk.
Room smelled bad, dirty carpet.
Reviewed on 24 Jun 2026
Pendry Chicago
Downtown Chicago
Price was £1,119, price is now £863 per person
£863
per person
2 Sept - 5 Sept
found 2 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,134 reviews)
The staff was very welcoming! The bellman greeted us by name the entire trip. Great location for shopping and the riverwalk. Highly recommend!
Reviewed on 23 Jun 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £1,136, price is now £899 per person
£899
per person
2 Sept - 5 Sept
found 2 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The hotel and location are beautiful but there needs to be much clearer signage as to where the entrance of the hotel is and the main lobby. Extremely confusing to travellers.
Reviewed on 23 Jun 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.
Omni Chicago Hotel
Downtown Chicago
Price was £1,504, price is now £1,208 per person
£1,208
per person
27 Aug - 31 Aug
found 11 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
Located in a walkable area near many Chicago attractions. We had a delicious breakfast in the hotel restaurant and the bar is nice. Room was large and comfortable
Reviewed on 23 Jun 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £1,897, price is now £1,495 per person
£1,495
per person
27 Aug - 31 Aug
found 11 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The hotel and location are beautiful but there needs to be much clearer signage as to where the entrance of the hotel is and the main lobby. Extremely confusing to travellers.
Reviewed on 23 Jun 2026
Don't see what you're looking for?
See all available trips from London to Central Chicago
View all tripsThings to do
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% 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.
