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.
Swissotel - Chicago
Downtown Chicago
£940
per person
24 Oct - 28 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Swiss hotel is very nice and the location is perfect! Gorgeous views and convenient to all the sights. It’s not a luxury hotel but for the price you can’t beat it. I highly recommend it.
Reviewed on 9 Aug 2026
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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
£1,477
per person
23 Sept - 27 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
This was an incredible experience, absolutely the best experience I’ve ever had with regards to accommodations. Our flight from Alaska landed at 9 am and we were at the hotel, exhausted, just looking for a place to put our bags before 10. We were given a six-hour early check-in at no charge. At checkout, our flight didn’t leave for five hours, so again, we asked for a place to put our bags, and were given a three-hour late checkout to accommodate our flight. No charge. The room was immaculate, the spa and fitness center were wonderful, and the view of the Chicago River and the historical buildings around the hotel are unparalleled. We will definitely be back.
Reviewed on 9 Aug 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.
Swissotel - Chicago
Downtown Chicago
£940
per person
24 Oct - 28 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Swiss hotel is very nice and the location is perfect! Gorgeous views and convenient to all the sights. It’s not a luxury hotel but for the price you can’t beat it. I highly recommend it.
Reviewed on 9 Aug 2026
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See all available trips from Dublin to Central Chicago
View all tripsThings to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
90% of travellers recommend
* 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.
