Des Plaines Vacations from $337

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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!

The Latest Des Plaines vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,785 reviews)
Their motto “natural and happy” really fits. The staff were pleasant and helpful and the natural touches like natural soaps and cucumber mint infused water made it a comfortable, happy place to stay. An oasis in a hot city.

Reviewed on Jul 4, 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
Aug 26 - Aug 31
found 2 days ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,950 reviews)
The property was very nice until we got to the room. The room seemed more dark and dingy. Very expensive for the quality of the room. Staff were extremely nice and the hotel was more central to different parks and modes of transportation.

Reviewed on Jul 2, 2025

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,755 reviews)
beautiful hotel, friendly and helpful staff.

Reviewed on Jul 2, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
The rooftop…which is mostly enclosed with lots of windows?

Reviewed on Jul 4, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,796 reviews)
Room was tiny for the price and no coffee maker in the room!

Reviewed on Jul 5, 2025

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Discover the most popular places to visit in Des Plaines

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 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

What to do in Des Plaines

River tour boat in Chicago

Architecture River Tour

$49
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$45
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Des Plaines

Des Plaines Hotel Deals

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
$260 nightly
The price is $300 total per night from Jul 7 to Jul 8
$300 total
Jul 7 - Jul 8
Total includes taxes and fees
9/10 Wonderful! (1,968 reviews)
"It was our first time in staying in Chicago and we couldnt have picked a better resort!!"

Reviewed on Jul 3, 2025

InterContinental Chicago Magnificent Mile by IHG
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $168 total per night from Aug 5 to Aug 6
$168 total
Aug 5 - Aug 6
Total includes taxes and fees
7.8/10 Good! (8,952 reviews)
"The location is amazing. Every staff member i had an encounter with was very kind and courteous. The elevators are amazing for an older hotel. So fast and efficient. This was our second stay there. When we go back to Chicago I plan on staying here."

Reviewed on Jul 3, 2025

Congress Plaza Hotel
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
$159 nightly
The price is $186 total per night from Jul 10 to Jul 11
$186 total
Jul 10 - Jul 11
Total includes taxes and fees
8.8/10 Excellent! (2,368 reviews)
"I would stay at this hotel again 100%"

Reviewed on Jul 3, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,858 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.

Find the Best Des Plaines Vacation Packages

Des Plaines Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
58,700
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Rosemont Theatre, Parkway Bank Park Entertainment District and Riviera Theatre

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Frequently asked questions

How much does a Des Plaines vacation package cost?
You'll find cheap prices from $337 on Expedia for your Des Plaines getaway. However, factors like the length of stay, the season 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'd like to score a cheap Des Plaines vacation package, consider visiting in November, December and January. You'll usually find better rates on flights and hotels during these months --- perfect for budget-conscious travelers.
How many days is enough for Des Plaines?
The ideal length of your Des Plaines vacation depends on what you'd like to do and see. Usually, a few days to a week will give you enough time to tick off all the leading attractions and explore some hidden treasures along the way.
How to find the best Des Plaines package deals?
Finding a cheap Des Plaines package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Des Plaines package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually 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. Click on the "Package" heading, then enter your destination and travel dates to see the best hotel prices and airfares. Bundling can save travelers 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 have your Des Plaines vacation dates finalized, book as early as you can to score some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Des Plaines?

  1. Choose when to go: Check your calendar and pack your bags. Your preferred season and the available activities will also help you decide when to visit Des Plaines.
  2. Set your budget: Consider costs such as transportation, flights and meals when calculating how much to set aside for your trip to Des Plaines. Then, pick a hotel that works with your budget, whether that's a wallet-friendly option or a more luxurious getaway.
  3. Explore Des Plaines using our trip planning tool: Gain insights into the most popular attractions and best stays for your trip to Des Plaines. You can also save your must-visit places, collaborate with family and friends and organize your plans in one place.
  4. Decide how long to go for: Now that you're more familiar with Des Plaines, you can figure out the perfect length of your break. Put together a rough plan and allocate enough time to cover everything you want to see.
  5. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Des Plaines vacation package that brings all your bookings together.
  6. Book any day trips or activities: Now to the fun part --- locking in everything you want to see and do. Browse some of the best things to do in Des Plaines and reserve your tickets in advance to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Des Plaines vacation packages?
Your Des Plaines trip is meant to be a relaxing escape from your daily routine, not a source of money worries. So to allow you more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.