Des Plaines Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $1,096 when you book a flight and hotel together*
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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.
DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
7.4/10 Good! (1,003 reviews)
I need the swimming pool...frowny-face Everything else is excellent

Reviewed on Jul. 31, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Great helpful staff! Very clean! Wonderful experience! Breakfast buffet is a must! So delicious

Reviewed on Jul. 31, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on Jul. 27, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,115 reviews)
The hotel is walkable to many restaurants. Nice neighborhood!

Reviewed on Jul. 31, 2025

Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
7.6/10 Good! (1,001 reviews)
Great place in Evanston. So close to everything.

Reviewed on Jul. 31, 2025

Ready to book your vacation to Des Plaines?

 

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Des Plaines Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Sep 1 to Sep 2
CA $186
CA $218 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (9,038 reviews)
"This was a nice option for my wife and I . Nice location plenty of dining with in walking distance. Highly recommend this hotel"

Reviewed on Jul. 29, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is CA $283 per night from Sep 1 to Sep 2
CA $283
CA $377 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (2,125 reviews)
"My two small daughters, 10 and under, and I were on a girls' trip to Chicago and stayed here. They were in awe of how friendly all the guests at the hotel were! Everyone was willing to share a fun fact of the city or just to welcome us. I also appreciated how easy it was to get to places, whether ..."

Reviewed on Jul. 29, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Aug 10 to Aug 11
CA $199
CA $234 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,549 reviews)
"Bed was very good. Staff was friendly and helpful."

Reviewed on Jul. 31, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,978 properties in Des Plaines
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Discover the most popular places to visit in Des Plaines

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

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.

Michigan Avenue
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Des Plaines

River tour boat in Chicago

Architecture River Tour

CA $57
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

CA $41
per adult
92% of travellers recommend
Skyline Lake Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

CA $62
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See all activities in Des Plaines

Frequently asked questions

How much does a Des Plaines vacation package cost?
You'll find cheap prices from CA $604 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.