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.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was £1,050, price is now £669 per person
£669
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Rooms are basic and bathrooms and sink area small. But all comfortable
Reviewed on 17 Aug 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,730, price is now £1,041 per person
£1,041
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
Loved the atmosphere and friendly atmosphere
Reviewed on 18 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,385, price is now £839 per person
£839
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.
Reviewed on 19 Aug 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was £1,580, price is now £984 per person
£984
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,359 reviews)
Shawn at the front desk was awesome. It was our first time in Chicago and we loved staying at LondonHouse!
Reviewed on 19 Aug 2025
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
Price was £1,263, price is now £806 per person
£806
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Friendly staff, clean and comfortable, convenient location
Reviewed on 20 Aug 2025
Don't see what you're looking for?
See all available trips from Dublin 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 £1,385, price is now £839 per person
£839
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.
Reviewed on 19 Aug 2025
Nobu Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was £3,261, price is now £2,623 per person
£2,623
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (707 reviews)
Great dining and drinking options in the neighborhood. Suite was comfortable, spacious and well designed. Awesome view of downtown.
Reviewed on 4 Aug 2025
Don't see what you're looking for?
See all available trips from Dublin 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 £1,266, price is now £862 per person
£862
per person
27 Oct - 30 Oct
found 1 day ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.
Reviewed on 19 Aug 2025
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was £1,464, price is now £1,008 per person
£1,008
per person
10 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Great spot, good location, nice rooms.
Reviewed on 20 Aug 2025
The Emily Hotel
Downtown Chicago
Price was £1,351, price is now £978 per person
£978
per person
10 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Rooms are basic and bathrooms and sink area small. But all comfortable
Reviewed on 17 Aug 2025
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.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was £675, price is now £445 per person
£445
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Staff were excellent, I needed to mail some parcels for a business event which they held for over a week (arrived earlier than expected!) breakfast was also excellent. Rooms were noisy, not from outside but from the other rooms. Walls must be thin and could hear conversation and the TV from both sides.
Reviewed on 20 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,385, price is now £839 per person
£839
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.
Reviewed on 19 Aug 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was £1,050, price is now £669 per person
£669
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Rooms are basic and bathrooms and sink area small. But all comfortable
Reviewed on 17 Aug 2025
Don't see what you're looking for?
See all available trips from Dublin 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.