West Side Cheap Holidays
Book a Cheap Hotel + Flight or Car together to unlock savings
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- Plan, book, travel with confidence
- 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 West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,554, price is now £1,020 per person
£1,020
per person
3 Jun - 7 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everyone that we encountered at the hotel was so helpful and so nice.
Reviewed on 11 Mar 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,534, price is now £1,715 per person
£1,715
per person
3 Jun - 9 Jun
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
One of the best hotels I've ever stayed at
Reviewed on 10 Mar 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was £2,000, price is now £1,386 per person
£1,386
per person
3 Jun - 9 Jun
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,613 reviews)
Clean room, perfect location
Reviewed on 11 Mar 2026
5* Cheap holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Downtown Chicago
Price was £1,552, price is now £1,380 per person
£1,380
per person
26 Apr - 30 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,003 reviews)
The room was a little dated. I was surprised that you didn’t have CNBC as a TV choice, I thought the gym was dated and the WiFi was inadequate
Reviewed on 28 Feb 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,534, price is now £1,715 per person
£1,715
per person
3 Jun - 9 Jun
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
One of the best hotels I've ever stayed at
Reviewed on 10 Mar 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was £1,843, price is now £1,480 per person
£1,480
per person
26 Apr - 30 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Nice bellmen, nice front staff, rooms were cozy and well kept. Everyone was very friendly and helpful. We would stay again.
Reviewed on 1 Mar 2026
3 Night Cheap holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was £981, price is now £804 per person
£804
per person
4 Jun - 7 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,575 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on 4 Mar 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was £1,329, price is now £924 per person
£924
per person
4 Jun - 7 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everyone that we encountered at the hotel was so helpful and so nice.
Reviewed on 11 Mar 2026
The Emily Hotel
Downtown Chicago
Price was £1,166, price is now £969 per person
£969
per person
4 Jun - 7 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,310 reviews)
Very cool, gorgeous hotel. The rooms offered a lot of amenities and had a fun industrial vibe. The bed was very comfortable, and we slept great! The staff was incredibly helpful. I would definitely stay at The Emily again.
Reviewed on 7 Mar 2026
4 Night Cheap holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was £1,087, price is now £853 per person
£853
per person
3 Jun - 7 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,575 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on 4 Mar 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,554, price is now £1,020 per person
£1,020
per person
3 Jun - 7 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everyone that we encountered at the hotel was so helpful and so nice.
Reviewed on 11 Mar 2026
The Emily Hotel
Downtown Chicago
Price was £1,384, price is now £1,093 per person
£1,093
per person
3 Jun - 7 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,310 reviews)
Very cool, gorgeous hotel. The rooms offered a lot of amenities and had a fun industrial vibe. The bed was very comfortable, and we slept great! The staff was incredibly helpful. I would definitely stay at The Emily again.
Reviewed on 7 Mar 2026
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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.
