Far Southeast Side Pet-friendly Holidays
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Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
€977
per person
24 Sept - 29 Sept
found 7 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (2,293 reviews)
Very clean and remodeled room. We enjoyed our stay and great location.
Reviewed on 17 Aug 2026
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Trump International Hotel & Tower Chicago
Downtown Chicago
€1,260
per person
5 Nov - 9 Nov
found 7 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.
Reviewed on 16 Aug 2026
Four Seasons Hotel Chicago
Downtown Chicago
€3,958
per person
24 Sept - 29 Sept
found 7 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around
Reviewed on 16 Aug 2026
Nobu Hotel Chicago
Downtown Chicago
€3,362
per person
8 Oct - 14 Oct
found 1 day ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.4/10 Exceptional! (897 reviews)
Rooms and beds are always so nice. Very calming and always get a good night’s sleep. I’ve always had a great experience. One detail which falls short is the toilet paper is very rough. Aside from this detail everything else surpasses my expectations.
Reviewed on 16 Aug 2026
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Hotel Riu Plaza Chicago
Downtown Chicago
€928
per person
5 Nov - 9 Nov
found 7 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I stayed here for about five days with my boyfriend. The hotel was very nice and the staff was very helpful. The rooftop is beautiful with a great view. It’s right in the middle of downtown so it’s very walkable to any places if you’re planning on spending a lot of time in the city. I would recommend finding parking offsite compared to the hotel because that’s what’s easiest if you are traveling via car a lot and also the food isn’t very great but it’s just fine. Overall, this was a very nice day and I would most definitely recommend it if you’re staying with a partner or family.
Reviewed on 17 Aug 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
€1,260
per person
5 Nov - 9 Nov
found 7 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.
Reviewed on 16 Aug 2026
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Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
88% of travellers recommend
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