Central Chicago Romantic Holidays

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Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
€1,542
per person
24 Nov - 28 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (1,012 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
€1,680
per person
24 Nov - 28 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
This was, by far, one of the best value-to-cost properties I've stayed with during a work trip. The rooms were clean, the complimentary breakfast was delicious, and the hotel was centrally located. Would definitely stay again!

Reviewed on 1 Oct 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
€1,633
per person
24 Nov - 28 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Downtown Chicago
€1,704
per person
24 Nov - 28 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,913 reviews)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
€1,554
per person
24 Nov - 28 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very good! (3,084 reviews)
Room was clean, bed was comfortable. The location is great but the room was tiny. There was only about 2 1/2 feet between the king bed and the walls so it was very cramped. No refrigerator, microwave or coffee maker in the room (there was a clothing steamer, which we didn't use, and a hair dryer in bathroom). Shower, not a tub, and new/extra towels were delivered on request. There are 3 elevators, but only one appeared to be working for the 3 nights we stayed. Coffee was available downstairs in the morning. There was a lot of street noise and sirens at night, but that may just be the city since we are used to a quieter neighborhood.

Reviewed on 1 Oct 2026

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

Four Seasons Hotel Chicago

Downtown Chicago
€2,506
per person
24 Nov - 28 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
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Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
€1,542
per person
24 Nov - 28 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (1,012 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
€1,680
per person
24 Nov - 28 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
This was, by far, one of the best value-to-cost properties I've stayed with during a work trip. The rooms were clean, the complimentary breakfast was delicious, and the hotel was centrally located. Would definitely stay again!

Reviewed on 1 Oct 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
€1,633
per person
24 Nov - 28 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (178 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

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

€34
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

€24
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Central Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.