Des Plaines Vacations

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    Save up to AED 148 when you book a flight and hotel together*

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Find the Best Des Plaines Vacation Packages

Des Plaines Hotel Deals

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
The price is AED 328 per night from Jan 5 to Jan 6
AED 328
AED 385 total
5 Jan - 6 January 2026
includes taxes & fees
8.8/10 Excellent! (3,608 reviews)
Spotless room, very nice staff

Reviewed on 29 December 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
The price is AED 482 per night from Jan 4 to Jan 5
AED 482
AED 657 total
4 Jan - 5 January 2026
includes taxes & fees
8.4/10 Very Good! (2,194 reviews)
Staff was great. Christmas decor was amazing.

Reviewed on 29 December 2025

Palmer House a Hilton Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is AED 449 per night from Jan 4 to Jan 5
AED 449
AED 635 total
4 Jan - 5 January 2026
includes taxes & fees
8.4/10 Very Good! (2,424 reviews)
Overall very clean and very friendly staff

Reviewed on 28 December 2025

Hilton Chicago
See all 5,110 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

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)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Navy Pier

Frequently asked questions

How do I find cheap flights to Des Plaines that have flexible change policies?
At Expedia, we've been channeling our inner yoga master to provide you with the most flexible airfares around. Simply check the "No change fee" box directly underneath the filter subheading "Flexible change policies" to find your ideal flight to Des Plaines.
Which airlines fly to Des Plaines?
Whether you prefer to sit in a premium seat or save your pennies in economy, these airlines will get you to or near Des Plaines:

  • United Airlines - 13,009 flights to or near Des Plaines each month, including 13,005 flights to O'Hare Intl. Airport (ORD) per month.
  • American Airlines - 10,036 flights to or near Des Plaines each month, including 10,036 flights to O'Hare Intl. Airport (ORD) per month.

How can I find cheap tickets to Des Plaines?
Book ahead of time, fly to or from nearby airports, avoid school vacation time — there are plenty of ways! Another one is to take advantage of Expedia's "flexible dates" function. Search for your Des Plaines flight, then check out the prices for nearby dates. In the last seven days, the lowest price for a flight to Des Plaines was .
How much is a flight to Des Plaines?
You could have locked in a return airfare to Des Plaines from anywhere between and in the last seven days. For one-way journeys departing from (), the lowest price during this period was just .
What are the most popular airports to fly into in Des Plaines?
Depending on which airline you book with and city of departure, one of these popular airports will be your entry point to Des Plaines:

  • O'Hare Intl. Airport (ORD) - 26,484 flights per month.
  • Midway Intl. Airport (MDW) - 6,439 flights per month.

When is the cheapest time to fly to Des Plaines?
Jet off on a Tuesday to boost your chances of landing the cheapest deal to Des Plaines. Mondays are usually the second most affordable day to take off. Saturday is generally the priciest day to fly anywhere.
How much is a plane ticket to Des Plaines?
In the last seven days, airfares ranged between and . Have a look at our terrific deals to Des Plaines, make a booking and get ready for your next fun vacation!
What months are the cheapest to book a flight to Des Plaines?
February is a cheap month to purchase a seat for your Des Plaines escape. Tickets are at a premium during the month of December, so keep clear of this time if possible.
How long is a flight to Des Plaines?
Your flight to Des Plaines could be short or long depending on where you set off from. Before you load your tablet with podcasts and audiobooks, take a look at the average flight times for these leading domestic routes:

  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 2 hours and 37 minutes
  • Denver, CO (DEN-Denver Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 34 minutes
  • Phoenix, AZ (PHX-Sky Harbor Intl.) to O'Hare Intl. Airport (ORD) - 3 hours and 17 minutes