Central Chicago Cheap Holidays

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Photo by Phil Ostroff
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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)
Excellent location. Could use some updated amenities-was there during a hot streak so a mini fridge would have been welcome.

Reviewed on 9 Aug 2026

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)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£1,397
per person
24 Oct - 30 Oct
found 5 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)
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5* Cheap holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,477
per person
23 Sept - 27 Sept
found 24 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
Beautiful room and view!

Reviewed on 9 Aug 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
Save 100% on your flight
£2,082
per person
24 Oct - 30 Oct
found 5 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,008 reviews)
Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
£3,135
per person
28 Sept - 2 Oct
found 23 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (891 reviews)
Don't see what you're looking for?
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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)
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)
Don't see what you're looking for?
See all available trips from Dublin to Central Chicago
View all trips

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

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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.