Leland Vacation Packages
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Top Leland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was CA $1,147, price is now CA $793 per person
CA $793
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Great view of the room. The staff were always willing to help and to provide.
Reviewed on May 5, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,813, price is now CA $1,855 per person
CA $1,855
per person
Jul 31 - Aug 3
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
Thank you to Javon who was super helpful in our check in . The staff was so nice and accommodating. Additional linens were delivered in less than 5 minutes and then even extended our check out to 1pm. I will definitely be back when I’m in Chicago to try to catch fireworks. Our corner room was outstanding and breathtaking
Reviewed on May 3, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $2,447, price is now CA $1,630 per person
CA $1,630
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (946 reviews)
Rooms were cleaned I liked how secure the hotel was.
Reviewed on Apr 29, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,583, price is now CA $1,072 per person
CA $1,072
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,144 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
The Royal Sonesta Chicago River North
Downtown Chicago
Price was CA $1,264, price is now CA $861 per person
CA $861
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,569 reviews)
Staff was amazing. Thank you for a great visit
Reviewed on May 5, 2026
Leland Hotel Deals
Grand Bear Resort at Starved Rock
2643 IL-178 Utica IL
The price is CA $155 per night from May 17 to May 18
CA $155
per night
May 17 - May 18
7.2/10 Good! (1,010 reviews)
The pool wasn't open the whole reason we went and still made us pay full after not really letting us know better. The jacuzzi didn't work ended up leaking everywhere they moved us in a nicer villa that they should have put us in the first place!
Reviewed on May 5, 2026
Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy
1879 N 2703rd Rd Ottawa IL
The price is CA $217 per night from May 7 to May 8
CA $217
per night
May 7 - May 8
9.8/10 Exceptional! (188 reviews)
All I can say is very peaceful & relaxing! I had the best sleep ever! I’m a very satisfied customer!
Reviewed on May 4, 2026
Home2 Suites by Hilton Dekalb
575 S ANNIE GLIDDEN RD DeKalb IL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Jun 3 to Jun 4
CA $185
per night
Jun 3 - Jun 4
9.2/10 Wonderful! (445 reviews)
Nice breakfast Enjoyed my room with the kitchen Helps travelers out.
Reviewed on May 3, 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.
