Uptown Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
- Level Chicago Fulton Market
Jun 27 - Jul 1Level Chicago Fulton Market + Flight
Downtown Chicago4 nights9.2/10 - Wonderful (482 reviews)"Yes"Reviewed May 12, 2026Roundtrip • Toronto (YTZ) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YYZ • NonstopCA $1,457CA $975found 18 hours agoper traveller - Swissotel - Chicago
Jul 28 - Aug 2Swissotel - Chicago + Flight
Downtown Chicago5 nights9.0/10 - Wonderful (3,332 reviews)"Very good Outstanding service "Reviewed May 19, 2026Roundtrip • Toronto (YYZ) - Chicago (ORD)YYZ - ORD • Nonstop ORD - YYZ • NonstopCA $3,626CA $1,987found 1 day agoper traveller - Sable at Navy Pier Chicago, Curio Collection by Hilton
Jul 28 - Aug 2Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago5 nights9.4/10 - Exceptional (2,507 reviews)"The restaurant is awful. The housekeeping service was very good. I had two meals in the restaurant and if the servers weren’t as nice as they were I would have sent them back.,,,,,, I should have sent them back. "Reviewed May 19, 2026Roundtrip • Toronto (YYZ) - Chicago (ORD)YYZ - ORD • Nonstop ORD - YYZ • NonstopCA $2,965CA $1,891found 1 day agoper traveller - LondonHouse Chicago, Curio Collection by Hilton
Jul 28 - Aug 2LondonHouse Chicago, Curio Collection by Hilton + Flight
Downtown Chicago5 nights9.4/10 - Exceptional (3,713 reviews)"Parking was easy. The hotel breakfast and regular menu was really good! Elevators were at times a little inconvenient, but nothing too bad "Reviewed May 19, 2026Roundtrip • Toronto (YYZ) - Chicago (ORD)YYZ - ORD • Nonstop ORD - YYZ • NonstopCA $3,410CA $2,288found 1 day agoper traveller - Hotel Felix River North/Magnificent Mile
Jul 28 - Aug 2Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago5 nights8.2/10 - Very good (2,705 reviews)"The room was clean but pretty basic. It was good overall but we did have an issue with the a/c switching off in the middle of the night. Unfortunately the hotel didn’t have any fans to remedy that situation. Other than that we had a very enjoyable stay. The location is great! "Reviewed May 19, 2026Roundtrip • Toronto (YYZ) - Chicago (ORD)YYZ - ORD • Nonstop ORD - YYZ • NonstopCA $2,379CA $1,605found 1 day agoper traveller
Uptown Hotel Deals
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from May 28 to May 29
CA $225
CA $257 total
May 28 - May 29
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Era perfecta para mi familia"
Reviewed on May 18, 2026
Days Inn by Wyndham Waukegan
630 N Green Bay Road Waukegan IL
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from Jun 7 to Jun 8
CA $106
CA $119 total
Jun 7 - Jun 8
includes taxes & fees
8.2/10 Very Good! (162 reviews)
"Good experience will choose for future"
Reviewed on May 18, 2026
Best Western Executive Inn Kenosha/Pleasant Prairie
7220 122nd Ave Kenosha WI
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from May 21 to May 22
CA $136
CA $161 total
May 21 - May 22
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"EVERYTHING WAS GREAT"
Reviewed on May 19, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.