Rutland Holidays
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Top Flight + Hotel Deals in Rutland
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was €507, price is now €359 per person
€359
per person
9 Jun - 11 Jun
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
The staff were extremely impressed and helpful. Help me with restaurant choices, where to go for tours. Only thing I regretted was not packing the proper clothes for the chance of weather. It was my personal birthday present to me and I did enjoyed myself.
Reviewed on 24 Apr 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was €752, price is now €543 per person
€543
per person
9 Jun - 11 Jun
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great staff, full kitchen and living room, good location, friendly people, safe. I would stay here again.
Reviewed on 23 Apr 2026
Chicago Marriott Downtown Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was €571, price is now €418 per person
€418
per person
9 Jun - 11 Jun
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (1,006 reviews)
The rooms are nice. I was a little disappointed to find out there would be a hold of 80 dollars each day on a credit card
Reviewed on 14 Apr 2026
Holiday Inn & Suites Chicago - Downtown by IHG
Downtown Chicago
Save 100% on your flight
Price was €575, price is now €425 per person
€425
per person
9 Jun - 11 Jun
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)
Staff and housekeeping were great! Location was convenient to the blue line. Would stay here again!
Reviewed on 23 Apr 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Save 100% on your flight
Price was €625, price is now €464 per person
€464
per person
9 Jun - 11 Jun
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,417 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, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.
Reviewed on 14 Apr 2026
Top hotels in Rutland
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is €124 per night from 24 May to 25 May
€124
24 May - 25 May
includes taxes & fees
9.4/10 Exceptional! (3,672 reviews)
Great location and hotel.
Reviewed on 24 Apr 2026
DoubleTree by Hilton Madison East
4402 E Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
The price is €100 per night from 3 May to 4 May
€100
3 May - 4 May
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
Very nice stop Staff warm and friendly. Great check in cookies.
Reviewed on 23 Apr 2026
Tru by Hilton Madison West, WI
8102 Watts Rd. Madison WI
Fully refundableReserve now, pay when you stay
The price is €80 per night from 20 May to 21 May
€80
20 May - 21 May
includes taxes & fees
9.4/10 Exceptional! (1,005 reviews)
This is a great facility. I totally recommend it!
Reviewed on 24 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.
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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.
