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

The Emily Hotel
Downtown Chicago
Price was €1,420, price is now €868 per person
€868
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on 22 Aug 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,918, price is now €1,155 per person
€1,155
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.
Reviewed on 25 Aug 2025

Pendry Chicago
Downtown Chicago
Price was €1,794, price is now €1,081 per person
€1,081
per person
4 Oct - 10 Oct
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.
Reviewed on 26 Aug 2025

The Royal Sonesta Chicago River North
Downtown Chicago
Price was €1,443, price is now €873 per person
€873
per person
4 Oct - 10 Oct
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Great location and room was fantastic! Only negatives were a lengthy check in and access to the outside deck was closed at 10 PM. Probably a good idea for that, but it would’ve been nice to go out there for a nightcap.
Reviewed on 26 Aug 2025

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

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,918, price is now €1,155 per person
€1,155
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.
Reviewed on 25 Aug 2025


The Langham, Chicago
Downtown Chicago
Price was €1,774, price is now €1,213 per person
€1,213
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on 12 Aug 2025
Price found within the past 48 hours. Click for updated prices.

Pendry Chicago
Downtown Chicago
Price was €1,436, price is now €1,130 per person
€1,130
per person
30 Oct - 2 Nov
found 13 hours ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.
Reviewed on 26 Aug 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,890, price is now €1,436 per person
€1,436
per person
30 Oct - 2 Nov
found 13 hours ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.
Reviewed on 25 Aug 2025

Level Chicago – Old Town
Downtown Chicago
Price was €1,352, price is now €1,133 per person
€1,133
per person
30 Oct - 2 Nov
found 13 hours ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9/10 Wonderful! (339 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on 27 Aug 2025
Price found within the past 48 hours. Click for updated prices.

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was €1,802, price is now €1,398 per person
€1,398
per person
10 Oct - 14 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (1,857 reviews)
The BEST part about our entire trip to Chicago was the friendly and helpful staff! The ONLY place in the whole city we encountered kind smiling people that went out of their way to help with anything! Roberto at the front desk deserves special recognition! I was trying to navigate to a nearby pizza place on foot and had three children with me and my GPS was NOT working at all the entire time I could find nothing; so I went to the front desk and Roberto was there with a smile and a super kind explanation about how it wasn’t my fault I couldn’t find anything and that the city being in layers messed up the GPS for everyone and it wasn’t just me! Then he took me outside and down the block to the corner to point out the street and turn I needed to take and made sure I understood and felt confident about going and we made it!! And that was NOT the way GPS was going to have me go (surprise surprise). All the bellmen were so nice and helpful and kept our luggage for us when we had an overlap in time and that allowed us to go see so many things on foot like the Art Institute and the Bean and shops! The valet was so fast and friendly, we expected to wait 20 minutes for our car and it was there in 5! We will DEFINITELY be staying again! The feeling of being safe and cared for are second to no other feeling when staying away from your own home; very well done and SO many thanks!
Reviewed on 27 Aug 2025

Viceroy Chicago
Downtown Chicago
Price was €1,839, price is now €1,450 per person
€1,450
per person
10 Oct - 14 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,071 reviews)
Close to everything. Gorgeous view of the lake and a beautiful rainbow. Wow!
Friendly staff.
Weird doors on the bathroom. Sliding doors tend to be noisy and unwieldy in general and this one was bad. That’s my only complaint.
Reviewed on 25 Aug 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €1,782, price is now €1,421 per person
€1,421
per person
10 Oct - 14 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Very nice hotel and staff were pleasant. The area is okay but if you go a block over it is nicer. The river walk is very close and inviting.
Reviewed on 25 Aug 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.