Rutland Vacation Packages
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Top Rutland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was CA $995, price is now CA $770 per person
CA $770
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,136 reviews)
Front desk staff are gems! They knew my name after 1 interaction and were very attentive. The room amenities were very nice-- espresso, bottled water, chocolates, steamer, toiletries.
Reviewed on Mar 1, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $2,415, price is now CA $1,714 per person
CA $1,714
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Property is excellent and always clean
Reviewed on Mar 7, 2026
Le Méridien Essex Chicago
Downtown Chicago
Price was CA $2,073, price is now CA $1,572 per person
CA $1,572
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.8/10 Excellent! (1,001 reviews)
Every activity I did was no further than 10 minutes away from the hotel.
Reviewed on Mar 7, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,282, price is now CA $986 per person
CA $986
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (2,070 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.
Reviewed on Mar 3, 2026
Rutland Hotel Deals
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $160 per night from Mar 8 to Mar 9
CA $160
CA $185 total
Mar 8 - Mar 9
includes taxes & fees
9.4/10 Exceptional! (3,539 reviews)
Governor’s club worth it - privacy
Reviewed on Mar 4, 2026
Best Western Plus InnTowner Madison
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Mar 8 to Mar 9
CA $152
CA $176 total
Mar 8 - Mar 9
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
clean room. I liked the walk in shower but my bathroom was very small & tight. (kept bumping my elbow into the glass shower door when using the toilet.)
Reviewed on Mar 5, 2026
La Quinta Inn & Suites by Wyndham Madison American Center
5217 E Terrace Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $97 per night from Mar 9 to Mar 10
CA $97
CA $112 total
Mar 9 - Mar 10
includes taxes & fees
8.2/10 Very Good! (1,429 reviews)
They were great
Reviewed on Mar 6, 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.
