
Orangeville Holidays
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Top Flight + Hotel Deals in Orangeville
Price found within the past 48 hours. Click for updated prices.


Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was €1,702, price is now €1,115 per person
€1,115
per person
2 Mar - 7 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing
Reviewed on 13 Jan 2026


Level Chicago – Old Town
Downtown Chicago
Price was €1,099, price is now €785 per person
€785
per person
2 Mar - 7 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay.
Reviewed on 12 Jan 2026
Top hotels in Orangeville

Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
The price is €101 per night from 6 Feb to 7 Feb
€101
6 Feb - 7 Feb
includes taxes & fees
8.8/10 Excellent! (856 reviews)
good deal
Reviewed on 12 Jan 2026

Super 8 by Wyndham Monroe WI
500 6th St and Hwy 69 Monroe WI
Fully refundableReserve now, pay when you stay
The price is €68 per night from 26 Jan to 27 Jan
€68
26 Jan - 27 Jan
includes taxes & fees
8.8/10 Excellent! (828 reviews)
Love this hotel, have stayed at it 3 times. You even get a discount at vinces just for staying at this hotel which is so kind of them
Reviewed on 7 Jan 2026

Baymont by Wyndham Freeport
1060 Riverside Dr Freeport IL
Fully refundableReserve now, pay when you stay
The price is €73 per night from 21 Jan to 22 Jan
€73
21 Jan - 22 Jan
includes taxes & fees
7.8/10 Good! (714 reviews)
Front desk staff was awesome, very professional, courteous and friendly, room was very clean bed was very comfortable
Reviewed on 1 Jan 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

