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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
£782
per person
1 Oct - 6 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very good! (2,879 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£1,064
per person
1 Oct - 6 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I had a great stay

Reviewed on 9 Aug 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£1,397
per person
24 Oct - 30 Oct
found 8 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Great staff, great place!

Reviewed on 5 Aug 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
£804
per person
1 Oct - 6 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very good! (2,089 reviews)
Swissotel - Chicago

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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5* Cheap holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
£1,415
per person
24 Oct - 28 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (891 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
Save 100% on your flight
£2,082
per person
24 Oct - 30 Oct
found 8 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,008 reviews)
Trump International Hotel & Tower Chicago

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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4 Night Cheap holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£751
per person
24 Oct - 28 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (149 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£861
per person
24 Oct - 28 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I had a great stay

Reviewed on 9 Aug 2026

Swissotel - Chicago

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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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£35
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Central Chicago

More 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.