Des Plaines Vacations from ￥292,470

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The Latest Des Plaines Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Great area: able to walk to many restaurants.

Reviewed on Aug 18, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
One of the best hotels. I will definitely stay here again.

Reviewed on Aug 16, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
Food options need more variety.

Reviewed on Aug 16, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
Great view of the lake and city

Reviewed on Aug 18, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.

Reviewed on Aug 17, 2025

Find the Best Des Plaines Vacation Packages

Des Plaines Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥27,686 per night from Sep 14 to Sep 15
￥27,686
￥32,502 total
Sep 14 - Sep 15
includes taxes & fees
7.8/10 Good! (8,963 reviews)
"Its location is the main reason why I chose to stay. The room has been updated; it is roomy and clean. Staffs are very friendly and helpful."

Reviewed on Aug 17, 2025

Congress Plaza Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥22,226 per night from Sep 1 to Sep 2
￥22,226
￥26,090 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,194 reviews)
"Staff was kind and friendly."

Reviewed on Aug 17, 2025

The Wade
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
The price is ￥23,646 per night from Aug 24 to Aug 25
￥23,646
￥27,757 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (4,717 reviews)
"Kids really enjoyed the pool. Breakfast was good as well"

Reviewed on Aug 17, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,923 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.

Discover the most popular places to visit in Des Plaines

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

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
Navy Pier featuring a sunset and rides

Navy Pier

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

Navy Pier

What to do in Des Plaines

River tour boat in Chicago

Architecture River Tour

￥6,122
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

￥6,646
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥5,981
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Des Plaines

Frequently asked questions

How much does a Des Plaines vacation package cost?
You'll find cheap prices from ￥292,470 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.