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Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,389, price is now CA $921 per person
CA $921
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The room was small, but fine. The bed was comfortable. The TV was too big so it covered the thermostat control panel, and the remote Guide button didn’t work. Also, the water pressure in the shower was super weak… glad I didn’t need to wash my hair.
But location, general vibe, and staff were great.
Reviewed on Jul 8, 2026

Four Seasons Hotel Chicago
Downtown Chicago
Price was CA $3,926, price is now CA $2,363 per person
CA $2,363
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
We came to the property for my wife’s 40th birthday celebration. From the moment we walked in through the doors, we felt pampered. Everyone on staff was friendly, high energy, and always willing to help. The housekeeping staff was top notch as they went above and beyond with expectation on not only keeping things clean, but organizing our clutter, leaving thoughtful birthday treats, and making us feel comfortable. I now do not want to travel without staying at a 4 seasons property. They made our experience 10 times better!
Reviewed on Jul 6, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,047, price is now CA $1,235 per person
CA $1,235
per person
Sep 24 - Sep 28
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back.
The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.
Reviewed on Jul 2, 2026
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Destination Geneva National
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Lodge Geneva National
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The French Country Inn Lake Geneva
W4190 West End Road Lake Geneva WI

Does your dog need a vacation? We are people and pet friendly!
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Como Cabana, Golf Cart, 2 Decks, Fire Pit, BBQ,
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Lakeside 5-bedrm/4bath home in Lake Como w/ paddleboards, kayaks, canoe by beach
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Hemlock Lake House
Lake Geneva WI

Huge home, sleeps 12, Newly remodeled, perfect for large groups NO PROM PARTIES
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Cozy Log Home
Lake Geneva WI
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.