Des Plaines Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by W. Ross Wells

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, 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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
The location was good. Staff was friendly. It was clean. But it was hard to enjoy time in the room because of the TV. They had horrible cable with nothing on, and it wasn’t a smart tv so we couldn’t log into any of our streaming services or even stream from our phones to the tv. We had to go out and buy a firestick.

Reviewed on Aug. 10, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Amazing property well worth the money

Reviewed on Aug. 11, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Great location with many great food and drink options. The room is a modern industrial design with unfinished walls and ceiling. It looks nice but not exactly my style. The room was clean and was comfortable for a two night stay.

Reviewed on Aug. 12, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (335 reviews)
A lot of good food options walkable distance.

Reviewed on Aug. 3, 2025

Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
7.6/10 Good! (1,003 reviews)
This property was right in the heart of downtown and right next to Northwestern - it's a perfect location, and was clean and comfortable!

Reviewed on Aug. 11, 2025

Ready to book your vacation to Des Plaines?

 

Choose your dates

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 $185 per night from Sep 1 to Sep 2
CA $185
CA $217 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,958 reviews)
"Super convenient to everything we needed or wanted Hotel is good, location is great"

Reviewed on Aug. 11, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Aug 21 to Aug 22
CA $239
CA $315 total
Aug 21 - Aug 22
includes taxes & fees
8.4/10 Very Good! (1,848 reviews)
"5 star rating! The vibe of the hotel is amazing and you can’t beat the location."

Reviewed on Aug. 11, 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Aug 26 to Aug 27
CA $217
CA $254 total
Aug 26 - Aug 27
includes taxes & fees
8.4/10 Very Good! (3,648 reviews)
"Good"

Reviewed on Aug. 10, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,928 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
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Des Plaines

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

Wrigley Field

4.5/5(158 reviews)

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

4.5/5(19 reviews)

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

4.5/5(459 reviews)

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
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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 $451 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.