
Countryside Holidays
Photo by Monica Ferro
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Top Flight + Hotel Deals in Countryside
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)
This property is beautiful and located in a great area.
Reviewed on 19 Aug 2025

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

Top hotels in Countryside

The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €151 per night from 1 Sept to 2 Sept
€151
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,213 reviews)
Great hotel and location!
"Everything about the stay was awesome. The service, the guys handling the bags, the rooms, the custodians, the view from the balacony and gym. Especially the speed bag in the gym! I highly recommend this hotel, it was great to see the fireworks at Navy pier from the balacony as well."
Reviewed on 23 Aug 2025

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €108 per night from 26 Aug to 27 Aug
€108
26 Aug - 27 Aug
includes taxes & fees
7.8/10 Good! (8,982 reviews)
"Experience what it must have felt like to attend the 1893 Worlds Fair"
Reviewed on 22 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €152 per night from 3 Sept to 4 Sept
€152
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,743 reviews)
"Great breakfast, good location."
Reviewed on 22 Aug 2025
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.
Popular places to visit

Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Countryside

Wendella's 90-min Chicago River Architecture Tour
€35
per adult
94% of travellers recommend

Chicago By Night River & Lake Cruise
€39
per adult
96% of travellers recommend
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