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
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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.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,014
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Room was ok, didn’t get the view I requested.
Some of the reception people was rude. Breakfast was adequate. No omellete bar,
Reviewed on Aug 29, 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
8/10 Very good! (10,207 reviews)
"Parking was a mess. The parking lot was full and they had to create a space for us to park. The parking lot is also prepay which we didn’t know nor were we told so we were charged a citation for not prepaying and luckily were not towed although three other hotel guests were not so lucky. When I mentioned ..."
Reviewed on Aug 29, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $199
CA $236 total
Aug 31 - Sep 1
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $324
CA $381 total
Sep 18 - Sep 19
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.
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.
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.
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 $62
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 $1,013 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.
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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.
