Des Plaines Vacations from $234

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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 Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $425, price is now $234 per person
$234
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,389, price is now $377 per person
$377
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)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,664, price is now $945 per person
$945
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
The best of the best. The largest rooms in town at the very best price with the very best experience.

Reviewed on Oct 26, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $444, price is now $261 per person
$261
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (3,105 reviews)
Location was great. Front desk staff were friendly and helpful

Reviewed on Oct 26, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $690, price is now $406 per person
$406
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)
The stay was everything I love the view and peaceful. Thank you

Reviewed on Oct 26, 2026

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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
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

$158
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
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
$119 nightly
The price is $140 total per night from Nov 24 to Nov 25
$140 total
Nov 24 - Nov 25
Total with taxes and fees
8.8/10 Excellent! (2,071 reviews)
"If going to Allstate for any reason best affordable stay"

Reviewed on Oct 26, 2026

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 22 to Nov 23
$124 total
Nov 22 - Nov 23
Total with taxes and fees
8/10 Very Good! (10,117 reviews)
"The building is architecturally beautiful. It needs major consideration on the interior such as the walls they elevators and improved the smell of the interior and it’s definitely overpriced."

Reviewed on Oct 26, 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
$122 nightly
The price is $145 total per night from Nov 22 to Nov 23
$145 total
Nov 22 - Nov 23
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
See all 5,038 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 $234 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.