Des Plaines Vacations from $115

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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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $232, price is now $115 per person
$115
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
great staff...loved our stay.

Reviewed on Nov 22, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $268, price is now $133 per person
$133
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city

Reviewed on Nov 26, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $676, price is now $341 per person
$341
per person
Feb 18 - Feb 22
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Everything was first class, even the coffee shop downstairs. Not to mention the grocery store that is attached to the same building. The ultimate convenience right near the miracle Mile in Chicago, my most favorite place in the world.

Reviewed on Nov 25, 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $355, price is now $184 per person
$184
per person
Feb 20 - Feb 22
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in.

Reviewed on Nov 25, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,397, price is now $740 per person
$740
per person
Dec 30 - Jan 4
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.

Reviewed on Nov 26, 2025

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Discover the most popular places to visit in Des Plaines

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
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

What to do in Des Plaines

Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$98
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
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
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Des Plaines

Des Plaines Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $108 total per night from Dec 7 to Dec 8
$108 total
Dec 7 - Dec 8
Total with taxes and fees
8.4/10 Very Good! (5,291 reviews)
All above.

Reviewed on Nov 24, 2025

Embassy Suites by Hilton Chicago Downtown River North
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
$83 nightly
The price is $98 total per night from Dec 7 to Dec 8
$98 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (3,400 reviews)
We enjoyed our stay at the Hilton Chicago. The room was clean and the staff was very nice. Housekeeping came and cleaned our room each morning which was amazing. We sat at the bar a few times during our stay and the drinks were great. We made it the hotel at 10 am and were allowed to check in early. ...

Reviewed on Nov 28, 2025

Hilton Chicago/Magnificent Mile Suites
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
$133 nightly
The price is $152 total per night from Dec 28 to Dec 29
$152 total
Dec 28 - Dec 29
Total with taxes and fees
8.4/10 Very Good! (2,103 reviews)
Excellent check in experience and follow up from Ella. The lobby bar area was beautiful with the Christmas trees and other decorations.

Reviewed on Nov 27, 2025

Palmer House a Hilton Hotel
See all 5,098 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 $115 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.