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 Fulton Market
Downtown Chicago
Price was CA $7,380, price is now CA $4,994 per person
CA $4,994
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.
Reviewed on Jul 8, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,290, price is now CA $1,614 per person
CA $1,614
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on Jul 9, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $3,176, price is now CA $2,335 per person
CA $2,335
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
View was beautiful, accommodations were excellent.
Reviewed on Jul 8, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,776, price is now CA $2,140 per person
CA $2,140
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
This hotel was located perfectly to see downtown Chicago. The rooms were beautiful and the staff was wonderful. We had booked some mobility scooters to get around downtown. We had no issues getting them up to our rooms.
Reviewed on Jul 9, 2026
Des Plaines Hotel Deals
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Jul 27 to Jul 28
CA $218
CA $259 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (1,721 reviews)
"Great location Lovely 🍸"
Reviewed on Jul 9, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $294 per night from Aug 9 to Aug 10
CA $294
CA $396 total
Aug 9 - Aug 10
includes taxes & fees
9.2/10 Wonderful! (1,886 reviews)
"The room was amazing! It was spacious and clean. The staff were helpful and very considerate. The hotel is located in an ideal location, right off of Michigan Avenue, in the heart of downtown. Shopping and restaurants are within short walking distances."
Reviewed on Jul 8, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $263 per night from Aug 6 to Aug 7
CA $263
CA $312 total
Aug 6 - Aug 7
includes taxes & fees
8/10 Very good! (10,213 reviews)
"Perfect location right across the park for a phenomenal price. Room was a little warm but the fan could keep the temp down thankfully."
Reviewed on Jul 9, 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 $35
per adult
88% 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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- 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.
