Des Plaines Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
CA $811
per person
Oct 28 - Oct 30
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
The property seems new and well kept. There are many amenities that enhance the stay including a pool, hot tub, basketball ball court, game room, sauna and steam room. We loved our stay.
Only negatives were there was not an ice machine, there was not daily cleaning service, the towels were OK and we needed our trash emptied but were many sure how to request that.
Overall a great spot. Affordable and lots of space with great views!
Reviewed on Aug 15, 2026
Swissotel - Chicago
Downtown Chicago
CA $1,132
per person
Oct 22 - Oct 25
found 6 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Always a great stay at The Swiss. Got upgraded to a corner room at no charge. Great views of the lake and the river. Paloma’s at the bar were great. Breakfast was awesome as well. Had the croissant sandwich and Belgian waffle.
Reviewed on Aug 17, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,501
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.
Reviewed on Aug 12, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
CA $1,843
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,384 reviews)
Broken elevator causing long lines and delays. Coffee set up in the lobby was awkward and $4 for a cup. Friends found bed bug in their bed. Staff very nice and good location.
Reviewed on Aug 16, 2026
Ready to book your vacation to Des Plaines?
Des Plaines Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $148
CA $176 total
Sep 8 - Sep 9
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $198
CA $236 total
Aug 30 - Aug 31
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $338
CA $397 total
Sep 12 - Sep 13
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.
Stay near popular Des Plaines attractions
Rivers Casino
8.0/10 (559 reviews)
Why not roll the dice with a visit to Rivers Casino during your travels in Des Plaines? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Lake Park
8.6/10 (80 reviews)
Commune with nature and explore the great outdoors at Lake Park during your travels in Des Plaines. Visit the shops and casinos in this family-friendly area.
Arndt Park
8.0/10 (44 reviews)
Explore the great outdoors at Arndt Park, a lovely green space in Des Plaines. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Harry H. Semrow Driving Range
8.0/10 (1 review)
You can take time to visit Harry H. Semrow Driving Range during your travels to Des Plaines. Check out the casinos and top-notch restaurants in this family-friendly area.
Apache Park
7.6/10 (40 reviews)
Explore the great outdoors at Apache Park, a lovely green space in Des Plaines. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
What to do in Des Plaines
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Des Plaines vacation package cost?
You'll find cheap prices from CA $811 on Expedia for your Des Plaines escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Des Plaines costs.
What are the cheapest months to go to Des Plaines?
If you're hoping to book a cheap Des Plaines vacation package, consider travelling in February, September and December. You'll typically find lower prices on hotels and airfares during these months — ideal for travellers wishing to save money.
How many days is enough for Des Plaines?
To fully enjoy a Des Plaines vacation, we suggest booking for 2 days. Divide your time between discovering Rivers Casino, Fashion Outlets of Chicago and other key sights, in addition to exploring neighbourhoods like O'Hare and Norwood Park. If you've got some time to spare, include a day trip or tour in your Des Plaines vacation itinerary.
How to find the best Des Plaines package deals?
Bagging a cheap Des Plaines package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most affordable Des Plaines package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Des Plaines vacation as a package?
You can enjoy significant savings on your next Des Plaines break by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Des Plaines?
If you're planning a spur-of-the-moment Des Plaines trip, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Des Plaines?
- Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Des Plaines.
- Set your budget: Consider costs such as flights, food and transportation when working out how much to set aside for your trip to Des Plaines. Then, select a hotel that works with your budget, whether that's an economical option or a swankier retreat.
- Determine how many days away: Start by listing all the sights and activities you want to get to in Des Plaines. Then, estimate how long you'll need for each, including any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a customized Des Plaines vacation package.
Explore a world of travel with Expedia
- Flights from Delhi (DEL) to Chicago (ORD)
- Flights from Denver (DEN) to Chicago (ORD)
- Flights from Milwaukee (MKE) to Chicago (ORD)
- Flights from Ottawa (YOW) to Chicago (ORD)
- Flights from Dallas (DFW) to Chicago (ORD)
- Flights from Kelowna (YLW) to Chicago (ORD)
- Flights from San Francisco (SFO) to Chicago (ORD)
- Flights from Québec (YQB) to Chicago (ORD)
- Flights to Chicago
- Flights from Charlottetown Alexander B. Campbell Airport (YYG) to Chicago (ORD)
- Flights from Buffalo (BUF) to Chicago (ORD)
- Flights from Ahmedabad (AMD) to Chicago (ORD)
- Flights from Moncton (YQM) to Chicago (ORD)
- Flights from Indianapolis (IND) to Chicago (ORD)
- Flights from Orlando (MCO) to Chicago (ORD)
- Flights from Fargo (FAR) to Chicago (ORD)
- Flights from Regina (YQR) to Chicago (ORD)
- Flights from Minneapolis (MSP) to Chicago (ORD)
- Flights from Victoria (YYJ) to Chicago (ORD)
- Flights from St. Louis (STL) to Chicago (ORD)
- Flights from Karachi (KHI) to Chicago (ORD)
- Flights from Grand Forks (GFK) to Chicago (ORD)
- Flights from Vancouver (YVR) to Chicago (ORD)
- Flights from Syracuse (SYR) to Chicago (ORD)
- Flights from Seattle (SEA) to Chicago (ORD)
- Flights from Burlington (BTV) to Chicago (ORD)
- Flights from Windsor (YQG) to Chicago (ORD)
- Flights from New York (LGA) to Chicago (ORD)
- Flights from Hamilton (YHM) to Chicago (ORD)
- Flights from Montreal (YUL) to Chicago (ORD)
- Flights from Atlanta (ATL) to Chicago (ORD)
- Flights from Toronto (YYZ) to Chicago (ORD)
- Flights from Kitchener (YKF) to Chicago (ORD)
- Flights from Detroit (DTW) to Chicago (ORD)
- Flights from Winnipeg (YWG) to Chicago (ORD)
- Flights from Washington (DCA) to Chicago (ORD)
- Flights from Los Angeles (LAX) to Chicago (ORD)
- Flights from Edmonton (YEG) to Chicago (ORD)
- Flights from Calgary (YYC) to Chicago (ORD)
- Flights from Halifax (YHZ) to Chicago (ORD)
- Flights from Miami (MIA) to Chicago (ORD)
- Flights from Waterloo (ALO) to Chicago (ORD)
- Flights from Houston (HOU) to Chicago (ORD)
- Flights from Bellingham (BLI) to Chicago (ORD)
- Flights from Thunder Bay (YQT) to Chicago (ORD)
- Flights to Rosemont
- Flights from Las Vegas (LAS) to Chicago (ORD)
- Flights from London (YXU) to Chicago (ORD)
- Flights from O'Hare Intl.
- Flights from Saskatoon (YXE) to Chicago (ORD)
- Flights from Philadelphia (PHL) to Chicago (ORD)
- Flights to O'Hare Intl.
- 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.
