
Chicago Pet-friendly Holidays
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Price found within the past 48 hours. Click for updated prices.

Kinzie Hotel
Downtown Chicago
Price was €569, price is now €434 per person
€434
per person
9 Jun - 11 Jun
found 10 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (2,105 reviews)
Very central location. The property is clean and the staff is welcoming. The rooms are clean and spacious.
Reviewed on 23 Apr 2026

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was €1,015, price is now €651 per person
€651
per person
8 Jun - 11 Jun
found 17 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (2,500 reviews)
Great location and very nice Hotel. Would stay there again!
Reviewed on 21 Apr 2026

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Save 100% on your flight
Price was €866, price is now €613 per person
€613
per person
8 Jun - 11 Jun
found 17 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (1,047 reviews)
This property is in a great location. The staff were friendly and the room was clean. The room we were in was very small and used. The building is really cool but we were super disappointed with it being under construction with no place to hang out and have a drink. We weren’t notified of the construction until right before our stay. We would have chosen somewhere else because of this.
Reviewed on 21 Apr 2026

L7 Chicago by LOTTE
Downtown Chicago
Price was €2,066, price is now €1,580 per person
€1,580
per person
11 Jun - 18 Jun
found 1 day ago
Return flight included
Málaga (AGP) to Chicago (ORD)
9.6/10 Exceptional! (3,910 reviews)
Great hotel, clean an super friendly staff.. would recommend
Reviewed on 22 Apr 2026

The Royal Sonesta Chicago River North
Downtown Chicago
Price was €813, price is now €699 per person
€699
per person
8 Jun - 11 Jun
found 17 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (2,530 reviews)
Room was very cold. Thermostat did not seem to be working.
Reviewed on 23 Apr 2026
Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Chicago
View all tripsPrice found within the past 48 hours. Click for updated prices.

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Save 100% on your flight
Price was €866, price is now €613 per person
€613
per person
8 Jun - 11 Jun
found 17 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (1,047 reviews)
This property is in a great location. The staff were friendly and the room was clean. The room we were in was very small and used. The building is really cool but we were super disappointed with it being under construction with no place to hang out and have a drink. We weren’t notified of the construction until right before our stay. We would have chosen somewhere else because of this.
Reviewed on 21 Apr 2026

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was €1,015, price is now €651 per person
€651
per person
8 Jun - 11 Jun
found 17 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (2,500 reviews)
Great location and very nice Hotel. Would stay there again!
Reviewed on 21 Apr 2026

The Royal Sonesta Chicago River North
Downtown Chicago
Price was €813, price is now €699 per person
€699
per person
8 Jun - 11 Jun
found 17 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (2,530 reviews)
Room was very cold. Thermostat did not seem to be working.
Reviewed on 23 Apr 2026
Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Chicago
View all trips
The Royal Sonesta Chicago River North
505 N State Street Chicago IL
Stay at this luxury hotel in Chicago. Enjoy free Wi-Fi, a 24-hour fitness centre and valet parking (surcharge). Our guests praise the pool and the restaurant ...
9.2/10 Wonderful! (2,549 reviews)
Room was very cold. Thermostat did not seem to be working.
Reviewed on 23 Apr 2026

Sports Illustrated Resorts Chicago
203 N Wabash Ave Chicago IL
Stay at this boutique hotel in Chicago. Enjoy free Wi-Fi, a 24-hour fitness centre and valet parking (surcharge). Our guests praise the helpful staff and the ...
9.2/10 Wonderful! (1,398 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, ...
Reviewed on 14 Apr 2026

Hilton Chicago
720 S Michigan Ave Chicago IL
Stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge) and a health club. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (2,745 reviews)
Staff were nice. Hotel was at maximum capacity per security and it just felt overwhelming and claustrophobic at times.
Reviewed on 22 Apr 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
