Rutland Holidays from £652
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Top Rutland Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was £896, price is now £652 per person
£652
per person
7 Nov - 11 Nov
found 18 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The staff were so welcoming! They knew it was our anniversary and we got showered with little nice surprises. Thank you so much for making our stay so memorable and meaningful. Our room was perfect, the lobby and the bar/lounge were beautiful and again the staff were great. Location is within 15 minute walk to every thing. We will definitely be back!
Reviewed on 31 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,543, price is now £1,036 per person
£1,036
per person
7 Nov - 11 Nov
found 18 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Place is great, staff, location.
So many great restaurants, river boats, shopping.
Loved our stay at Trump International
Reviewed on 31 Aug 2025
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was £1,411, price is now £960 per person
£960
per person
10 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,096 reviews)
I booked a king room, & was asked about upgrading to a king room on the top floor with a city view for a small fee. I agreed, and upon going to our new room we quickly found out the toilet would not flush. We went back down (maybe 30mins after we checked in) to inform them of the issue, & were told no one could fix it so we were downgraded to a queen room (not offered our original king booking). other than this, the facility was nice/clean enough and the staff was great. Still very close to shopping but was one of the quietest streets i’ve stayed on in chicago.
Reviewed on 30 Aug 2025
L7 Chicago by LOTTE
Downtown Chicago
Save 100% on your flight
Price was £1,582, price is now £1,080 per person
£1,080
per person
10 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (2,866 reviews)
Great staff and very easy to get around
Reviewed on 31 Aug 2025
The Emily Hotel
Downtown Chicago
Price was £1,208, price is now £850 per person
£850
per person
7 Nov - 11 Nov
found 18 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,192 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
Rutland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Dane County Regional Airport (MSN) |
Population | 2,100 |
Max Temp Winter | -3.89ºC |
Max Temp Summer | 24ºC |
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 £145 per night from 10 Sept to 11 Sept
£145
10 Sept - 11 Sept
includes taxes & fees
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is £56 per night from 14 Sept to 15 Sept
£56
14 Sept - 15 Sept
includes taxes & fees
AmericInn by Wyndham Madison West
516 Grand Canyon Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is £69 per night from 2 Sept to 3 Sept
£69
2 Sept - 3 Sept
includes taxes & fees
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. Flight-inclusive packages are ATOL protected.