Des Plaines Vacations from ¥311,696

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The Latest Des Plaines Vacation Packages

Price found within the past 48 hours. Click for updated prices.
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
¥311,696
per person
Nov 9 - Nov 13
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (3,352 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥375,400
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥374,042
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Level Chicago - River North

Level Chicago - River North

Downtown Chicago
¥398,572
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
Clean. On site laundry was awesome.

Reviewed on Oct 6, 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥530,538
per person
Nov 9 - Nov 13
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)

Find the Best Des Plaines Vacation Packages

Des Plaines Hotel Deals

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

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

3001 South Mannheim Road Des Plaines IL
Fully refundable
¥20,722
¥24,447 total
Oct 25 - Oct 26
includes taxes & fees
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
¥18,332
¥21,794 total
Nov 4 - Nov 5
includes taxes & fees
Congress Plaza Hotel
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
¥25,412
¥30,211 total
Oct 25 - Oct 26
includes taxes & fees
River Hotel
See all 4,933 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.

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.
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Lake Park

8.6/10 (80 reviews)
Lake Opeka's sparkling waters anchor this recreational haven with scenic walking paths and wildlife. Visitors can sail, fish, golf the par-3 course, or enjoy lakeside picnics in this family-friendly retreat.
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Arndt Park

8.0/10 (44 reviews)
This community park offers sports courts, playgrounds, and a popular winter sled hill illuminated until 10 PM. Reserve picnic pavilions for gatherings or simply enjoy the seasonal recreational spaces year-round.
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Apache Park

7.6/10 (40 reviews)
Apache Park features innovative playgrounds, fitness equipment, and community-created Peace Poles in a colorful, accessible design. Explore the walking paths and outdoor exercise stations for an active family outing.
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Harry H. Semrow Driving Range

8.0/10 (1 review)
This spacious facility boasts 73 driving range stalls and a beautifully landscaped 18-hole mini golf course. Perfect for both serious golfers perfecting their swing and families enjoying a recreational outing together.
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What to do in Des Plaines

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥3,812
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

¥6,275
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

¥6,642
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Des Plaines

Frequently asked questions

How much does a Des Plaines vacation package cost?
You'll find cheap prices from ¥311,696 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?
You can usually find lower rates and better availability in February, September and December. Explore our cheap Des Plaines vacation packages and you could score some excellent off-season deals.
How many days is enough for Des Plaines?
The ideal duration for your Des Plaines vacation depends on what you'd like to see. Generally, a few days to a week will give you enough time to visit all the top attractions and explore some hidden spots 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 travel: Check your schedule and pack your bags. Your preferred time of year and the activities available will also help you decide when to escape to Des Plaines.
  2. Plan your budget wisely: As well as the price of your hotel, you should factor in other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Des Plaines.
  3. Decide how many days away: Start by making a list of all the activities and sights you want to get to in Des Plaines. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your airfare and accommodations: Once you've settled on your trip dates and duration, book the right Des Plaines vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.