
Dyer Vacation Packages
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Save up to CA $1,096 when you book a flight and hotel together*
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Your Dyer Vacation
Organizing your next epic break is a piece of cake with a Dyer vacation package. The neighborhood of Glenwood, which is good for golfing, makes a good starting point to uncover the delights of this vibrant city. Midwest Training & Ice Center is one of the top attractions to check off your itinerary during a trip to Dyer. Browse Expedia's wide range of travel options and begin planning your ultimate vacation to Dyer now.
Top Dyer Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Level Chicago – Old Town
Downtown Chicago
Price was CA $1,254, price is now CA $794 per person
CA $794
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on Aug. 27, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,066, price is now CA $1,229 per person
CA $1,229
per person
Oct 30 - Nov 2
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on Aug. 29, 2025

Pendry Chicago
Downtown Chicago
Price was CA $1,883, price is now CA $1,120 per person
CA $1,120
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.
Reviewed on Aug. 26, 2025


Level Chicago - River North
Downtown Chicago
Price was CA $1,634, price is now CA $1,060 per person
CA $1,060
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (672 reviews)
The hotel never got cool, hot everywhere, even the community areas. We had to use the TV in the communal area as ours didn't work. We called on day one and the girl laughed and never sent anyone to fix it. Our key cards didn't work multiple times during the stay. The party that happened at the pool on Sunday night of our stay was awful. I couldn't imagine what my kids saw even those this hotel said no parties.
Reviewed on Aug. 25, 2025
Dyer Hotel Deals

Hilton Chicago/Oak Lawn
9333 S Cicero Ave, Oak Lawn, IL
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Sep 14 to Sep 15
CA $175
CA $201 total
Sep 14 - Sep 15
includes taxes & fees

Baymont by Wyndham Chicago/Alsip
12801 South Cicero, Alsip, IL
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Sep 7 to Sep 8
CA $126
CA $143 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very Good! (1,004 reviews)
"Really nice place. The pet friendly room was nice."
Reviewed on Aug. 23, 2025

Ameristar Casino Hotel East Chicago
777 Ameristar Blvd., East Chicago, IN
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Sep 1 to Sep 2
CA $138
CA $169 total
Sep 1 - Sep 2
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.
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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.