Hometown Vacation Packages
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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.
La Banque Hotel
Price was CA $1,259, price is now CA $829 per person
CA $829
per person
May 25 - May 29
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (469 reviews)
Room was amazing and beautiful and comfortable
Only issue was when we arrived they had a plumbing issue and the whole place smelled horrific like a sewer. We didn’t go eat at the restaurant because the smell made us nauseous
Reviewed on Mar 1, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,878, price is now CA $1,207 per person
CA $1,207
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
Beautiful room. Property upgraded to 2-bedroom. Facilities are great with huge gym. Great stay in Chicago.
Reviewed on Mar 14, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $3,917, price is now CA $2,572 per person
CA $2,572
per person
May 2 - May 8
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Nice bellmen, nice front staff, rooms were cozy and well kept. Everyone was very friendly and helpful. We would stay again.
Reviewed on Mar 1, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,755, price is now CA $1,160 per person
CA $1,160
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
ALL the employees were nice, went out of their way to help and property was clean too!
Reviewed on Mar 16, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,512, price is now CA $1,051 per person
CA $1,051
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Rooms clean friendly staff best location
Reviewed on Mar 16, 2026
Hometown Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Apr 1 to Apr 2
CA $133
CA $156 total
Apr 1 - Apr 2
includes taxes & fees
8/10 Very Good! (9,947 reviews)
Beautiful spacious room with a great view of the lake. The property is old so don’t expect the building to be pristine. My only issue and the only thing I would tell you to keep in mind is that it can be very loud with street noise and the walls are extremely thin. We heard the very loud people in ...
Reviewed on Mar 16, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from Mar 22 to Mar 23
CA $181
CA $251 total
Mar 22 - Mar 23
includes taxes & fees
9.4/10 Exceptional! (3,541 reviews)
ALL the employees were nice, went out of their way to help and property was clean too!
Reviewed on Mar 16, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Mar 23 to Mar 24
CA $179
CA $210 total
Mar 23 - Mar 24
includes taxes & fees
8.6/10 Excellent! (5,750 reviews)
Clean room
Reviewed on Mar 16, 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.
Discover the most popular places to visit in Hometown
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Hometown
Wendella's 90-min Chicago River Architecture Tour
CA $55
per adult
94% of travellers recommend
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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.
