Des Plaines Vacations from $235

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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 Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was $402, price is now $235 per person
$235
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,334 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,440, price is now $428 per person
$428
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
My experience at the Sheraton was terrible. I was assigned a room right next to the elevator, where there was also a shared microwave for guests on the floor. A large group of young people was placed in the same hallway. They appeared to be intoxicated and made excessive noise from around 11 p.m. until nearly 4 a.m., making it impossible to sleep. I called the front desk three times asking for help, but the noise continued and nothing was resolved. I felt very unsafe and completely let down by the hotel staff. Guests should be able to expect a restful stay and a response when they ask for help. I left exhausted and deeply disappointed. I expected much better from the Sheraton.

Reviewed on Oct 28, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $518, price is now $300 per person
$300
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
Great staff they accommodating us.

Reviewed on Oct 30, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $648, price is now $377 per person
$377
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Super clean. Super views. Super amenities. Will stay again.

Reviewed on Oct 26, 2026

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Price was $1,110, price is now $685 per person
$685
per person
Dec 16 - Dec 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (1,005 reviews)

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Stay near popular Des Plaines attractions

Rivers Casino

8.0/10 (559 reviews)
Chicagoland's premier casino offers over 1,000 slots and nearly 50 table games in a vibrant setting. Enjoy upscale dining at Hugo's Frog Bar & Chop House while taking advantage of the free on-site parking.
See properties

What to do in Des Plaines

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago's Navy Pier Centennial Wheel Ticket

Chicago's Navy Pier Centennial Wheel Ticket

$24
per adult
100% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
See all activities in Des Plaines

Des Plaines Hotel Deals

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

3 out of 5
3001 South Mannheim Road Des Plaines IL
Fully refundable
$123 nightly
The price is $145 total per night from Nov 29 to Nov 30
$145 total
Nov 29 - Nov 30
Total with taxes and fees
Holiday Inn Express & Suites Chicago O'Hare Airport 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
$104 nightly
The price is $124 total per night from Nov 10 to Nov 11
$124 total
Nov 10 - Nov 11
Total with taxes and fees
8/10 Very Good! (10,061 reviews)
"very bad and vintage looking room, AC was antique, throwing dust, poor lighting, over all very bad experience."

Reviewed on Oct 30, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $159 total per night from Nov 2 to Nov 3
$159 total
Nov 2 - Nov 3
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
See all 5,017 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 $235 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.

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