Hometown Vacation Packages
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- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Your Hometown Vacation
An easy way to experience this city is with a customized Hometown vacation package. Base yourself in the neighborhood of The Loop, which is great for bars and pubs, history and festivals or go someplace else — our package deals are all about you. Eager to venture out and explore? SeatGeek Stadium, Chicago Ridge Shopping Mall and Trinity Christian College are just a few of the most popular places to visit during your trip to Hometown. Browse Expedia's wide range of travel options and start organizing your ultimate vacation to Hometown today.
Top Hometown Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was CA $3,076, price is now CA $2,269 per person
CA $2,269
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
My only suggestions. The batteries in the rechargeable TV remotes die too quickly and the room service ordering software on the tablet was lacking pictures. Options for an omelet were red and unavailable to select. So unless they were out of eggs, that was an issue. And the bedside tablet nightlight is nice, but too bright. These were a struggle to come up with because the service was impeccable.
Reviewed on Oct 30, 2026
Hometown Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Nov 10 to Nov 11
CA $162
CA $193 total
Nov 10 - Nov 11
includes taxes & fees
8/10 Very good! (10,061 reviews)
"very bad and vintage looking room, AC was antique, throwing dust, poor lighting, over all very bad experience."
Reviewed on Oct 30, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Nov 2 to Nov 3
CA $187
CA $223 total
Nov 2 - Nov 3
includes taxes & fees
8/10 Very good! (2,621 reviews)
"Everything was perfect"
Reviewed on Oct 30, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Nov 23 to Nov 24
CA $166
CA $198 total
Nov 23 - Nov 24
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.
What to do in Hometown
Skydeck Chicago at Willis Tower
CA $60
per adult
84% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
Frequently asked questions
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- Unity Temple
- Centennial Beach
- Garfield Park Conservatory
- Lincoln Park Zoo
- Chicago Riverwalk
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- Robie House
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- Art Institute of Chicago
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- Navy Pier
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- Chicago Theatre
- Buckingham Fountain
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- Willis Tower
- 875 North Michigan Avenue
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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.
