Des Plaines Vacation Packages
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Your Des Plaines Vacation
Reserve a Des Plaines vacation package that includes everything you need and nothing you don't. Good for cafes, nature and bars and pubs, think about basing yourself in the neighborhood of Rogers Park. If your trip to Des Plaines includes a little sightseeing, don't miss major attractions such as Allstate Arena, Rosemont Theatre and Fashion Outlets of Chicago. Stop dreaming and start adventuring. Explore the many options on Expedia today and finally put your Des Plaines vacation plans into motion!
Top Des Plaines Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $3,635, price is now CA $2,437 per person
CA $2,437
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,606, price is now CA $1,100 per person
CA $1,100
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,401, price is now CA $983 per person
CA $983
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026
Des Plaines Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Jun 30 to Jul 1
CA $194
CA $230 total
Jun 30 - Jul 1
includes taxes & fees
8/10 Very good! (10,140 reviews)
"4 days of a cold shower and a broken bed. I will never stay here again and I suggest that anyone thinking about staying here to look elsewhere. Bathrooms were severely outdated."
Reviewed on Jun 27, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Jul 5 to Jul 6
CA $217
CA $305 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (1,830 reviews)
"Best location on Michigan Avenue"
Reviewed on Jun 27, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Jul 6 to Jul 7
CA $239
CA $284 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (4,467 reviews)
"The housekeeper was always so friendly and did such a great job. Honestly, all the staff was fantastic and so helpful."
Reviewed on Jun 27, 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.
Stay near popular Des Plaines attractions
What to do in Des Plaines
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
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- Visit Rosemont
- Unity Temple
- Navy Pier
- Visit Downtown Chicago
- Chicago Vacations
- Visit The Loop
- Water Tower Place
- Golf Vacations
- International Museum of Surgical Science
- Garfield Park Conservatory
- Visit Elk Grove Village
- Ernest Hemingway Museum and House
- Chicago Riverwalk
- Northwestern University
- Grant Park
- Marina City
- Lincoln Park Zoo
- Downtown Chicago Vacations
- Buckingham Fountain
- Lakeview Vacations
- Six Flags Great America
- United Center
- Frank Lloyd Wright Historic District
- Willis Tower
- Centennial Beach
- Wrigley Field
- Legoland® Discovery Center
- Chicago Theatre
- Art Institute of Chicago
- Montrose Beach
- Rosemont Vacations
- Millennium Park
- Woodfield Mall
- 875 North Michigan Avenue
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
