Cheap flights To Des Plaines (CHI) from $29

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Cheap Flights to Des Plaines from $29 One Way, $63 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Jan 14 - Wed, Jan 14
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jan 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Jan 14, priced at $63 found 1 day ago
Tue, Dec 9 - Wed, Dec 10
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 12 hours ago
$63
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Tue, Dec 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Dec 10, priced at $63 found 12 hours ago
Tue, Nov 18 - Tue, Nov 18
LGA
LaGuardia
ORD
O'Hare Intl.
$63 Roundtrip, just found
$63
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Nov 18 from LaGuardia to O'Hare Intl., returning Tue, Nov 18, priced at $63 just found
Thu, Jan 8 - Mon, Jan 12
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$64 Roundtrip, found 6 days ago
$64
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Jan 8 from Dallas-Fort Worth Intl. to Midway Intl., returning Mon, Jan 12, priced at $64 found 6 days ago
Tue, Dec 9 - Tue, Dec 16
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$68 Roundtrip, found 2 hours ago
$68
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Dec 9 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Dec 16, priced at $68 found 2 hours ago
Thu, Jan 22 - Mon, Jan 26
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Jan 22 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Jan 26, priced at $68 just found
Thu, Nov 13 - Mon, Nov 17
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$87 Roundtrip, just found
$87
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Nov 13 from Newark Liberty Intl. Airport to O'Hare Intl., returning Mon, Nov 17, priced at $87 just found
Thu, Feb 19 - Sun, Feb 22
DAL
Love Field
MDW
Midway Intl.
$117 Roundtrip, found 11 hours ago
$117
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Thu, Feb 19 from Love Field to Midway Intl., returning Sun, Feb 22, priced at $117 found 11 hours ago
Fri, Jan 9 - Sun, Jan 11
DAL
Love Field
ORD
O'Hare Intl.
$117 Roundtrip, found 15 hours ago
$117
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Fri, Jan 9 from Love Field to O'Hare Intl., returning Sun, Jan 11, priced at $117 found 15 hours ago
Thu, Feb 19 - Sun, Feb 22
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$117 Roundtrip, found 11 hours ago
$117
Roundtrip
found 11 hours ago
Select United flight, departing Thu, Feb 19 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sun, Feb 22, priced at $117 found 11 hours ago

Des Plaines Flight Information

Traveling To
Des Plaines
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, Southwest Airlines, United
Flight Price
$63
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Des Plaines economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago Downtown
4.0-star property

The Royal Sonesta Chicago Downtown

Dec 14 - Dec 17

3 night stay

Boston (BOS) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $383, price is now $250 per person
$250
per person
found 2 days ago
The Westin Michigan Avenue Chicago
4.5-star property

The Westin Michigan Avenue Chicago

Dec 10 - Dec 12

2 night stay

Boston (BOS) to Chicago (ORD)

Delta • Coach

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Coach
Price was $633, price is now $268 per person
$268
per person
found 1 day ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Dec 26 - Dec 30

4 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Boston (BOS)

United • Coach
Price was $790, price is now $535 per person
$535
per person
found 1 day ago
Don't see what you're looking for?
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Des Plaines premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Warwick Allerton - Chicago
4.0-star property

Warwick Allerton - Chicago

8.4/10 Very Good! (2,921 reviews)

Dec 6 - Dec 10

4 night stay

New York (NYC) to Chicago (ORD)

Frontier Airlines • PremiumEconomy

Chicago (ORD) to New York (NYC)

Spirit Airlines • PremiumEconomy
Price was $511, price is now $412 per person
$412
per person
found 1 day ago
This was a great place to say. The room was spacious, nice, and clean. There was both hotel valet parking and valet parking next door. The hotel was conveniently located for shopping along Michigan avenue, small restaurants on side streets, and a Starbucks. Since the area included Northwestern University and hospitals, it was safe. I hope to stay at Warwick Allerton again.

Reviewed on Oct 23, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,602 reviews)

Dec 5 - Dec 7

2 night stay

Minneapolis (MSP) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Price was $624, price is now $469 per person
$469
per person
found 1 day ago
One day didn’t receive room service

Reviewed on Sep 2, 2025

Arlo Chicago
4.0-star property

Arlo Chicago

9.2/10 Wonderful! (1,852 reviews)

Dec 6 - Dec 10

4 night stay

New York (NYC) to Chicago (ORD)

Frontier Airlines • PremiumEconomy

Chicago (ORD) to New York (NYC)

Spirit Airlines • PremiumEconomy
Price was $649, price is now $513 per person
$513
per person
found 1 day ago
Super convinient and great location.

Reviewed on Oct 25, 2025

Don't see what you're looking for?
See all available trips from New York to Des Plaines
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Des Plaines first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Wade
4.5-star property

The Wade

8.4/10 Very Good! (1,370 reviews)

Dec 28 - Jan 2

5 night stay

New York (NYC) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,066, price is now $847 per person
$847
per person
found 10 hours ago
We loved the breakfast options and the service. Everyone was very friendly and efficient.

Reviewed on Oct 26, 2025

Arlo Chicago
4.0-star property

Arlo Chicago

9.2/10 Wonderful! (1,852 reviews)

Dec 28 - Jan 2

5 night stay

New York (NYC) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,127, price is now $853 per person
$853
per person
found 10 hours ago
Super convinient and great location.

Reviewed on Oct 25, 2025

Springhill Suites by Marriott Chicago Downtown/ River North
3.5-star property

Springhill Suites by Marriott Chicago Downtown/ River North

9.2/10 Wonderful! (1,007 reviews)

Dec 28 - Jan 2

5 night stay

New York (NYC) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,079, price is now $901 per person
$901
per person
found 10 hours ago
Great location and friendly staff.

Reviewed on May 14, 2025

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Frequently asked questions

Which airlines fly to Des Plaines?
Take your pick of 20 airlines that fly into O'Hare Intl. Airport (ORD), the leading airport in the city. With all those options, you're certain to walk away with a terrific deal. Here are some of the best international airlines that'll get you to Des Plaines — and then exploring every nook and cranny of this city:

  • United Airlines - 612 flights to Des Plaines per month
  • American Airlines - 339 flights to Des Plaines per month
  • Air Canada - 190 flights to Des Plaines per month

What is the best airport to fly to in Des Plaines?
O'Hare Intl. Airport (ORD), around 4 miles south of downtown Des Plaines, is one choice. Midway Intl. Airport (MDW) is another. Compare the flight deals to both airports, along with which terminal may be more convenient for you.
How much is a flight to Des Plaines?
Last week, prices fluctuated between $63 and $117 for a round-trip fare to Des Plaines. One-way fares originating from New York (EWR) dipped to a low $29 during the same time period.
How to book the cheapest flight to Des Plaines?
With some of the most incredible flight deals around, you'll get more for your money with Orbitz. The following tips and hints will help you snap up cheap flights to Des Plaines — and leave you with more money in your pocket:

  • Taking off from or arriving at nearby airports can be cheaper. Enter your preferred departure and arrival airports. Next, select the 'Nearby airports' function below to look through your options.
  • If your plans aren't cast in stone, click on the 'Show flexible dates' link to browse flight deals for multiple departure dates. If you find a suitable cheaper fare, go with it.
  • To filter your results, click on 'Show options.' You can search based on airlines, seating class, nonstop flights and refundable flights. You can also select whether you want to fly in the morning, afternoon or evening under 'Sort & Filter' to the left.
  • The early bird gets the most rewarding deals, so book as soon as you've worked out your travel dates. The most affordable fares get snapped up fast and prices generally climb as the departure date nears.
  • Combine your flights, hotels and car rental into a value-for-money package deal. Save your hard-earned money for things that really excite you, like discovering every corner of Des Plaines.
  • Flying during peak season can mean steep airfares. Try to plan your trip outside of popular periods, such as Christmas, New Year's Eve and Easter.

How long is a flight to Des Plaines?
The United States is big, so that depends on where you're departing from. To make vacation planning a bit easier, we've selected three of the top routes to Des Plaines and worked out their average flight times:

  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 2 hours and 40 minutes
  • Boston, MA (BOS-Logan Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 51 minutes
  • Washington, DC (DCA-Ronald Reagan Washington National) to O'Hare Intl. Airport (ORD) - 2 hours and 13 minutes

What is the best time to book a flight to Des Plaines?
If you can, book your flights to Des Plaines in January. This is the best month to score low airfares, followed by February and August. With a bit of organizing, you're sure to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to Des Plaines?
In general, Tuesdays, Wednesdays and Saturdays are the cheapest days to book flights to Des Plaines. If you're looking for unbeatable airfares, search across those days and you're likely to score a terrific flight deal.
What is the cheapest day of the week to fly to Des Plaines?
If you're searching for cheap flights to Des Plaines, depart early in the week. Orbitz data from 2020 shows Monday is the cheapest day to fly out, followed by Tuesday. Saturday has the most expensive fares, so avoid this day and do your wallet a favor.
What is the cheapest month to fly to Des Plaines?
Jet off in August if you're sticking to a budget. Orbitz data shows that this is generally the best month for cheap flights to Des Plaines. June is when ticket prices really go up.
Which airlines allow free cancellation?
When searching for flights on Orbitz, click on "Filter by flexible change policies." This filter will quickly find all the carriers offering free cancellation and no change fees. That means you can relax knowing that if things unexpectedly change, your ticket can too.
What do I need for the flight to Des Plaines?
The secret to a successful flight is to prepare well. Listed below are some tips that'll help get you ready for your adventure:

  • Before you board the plane, you'll need to present a valid form of government ID, like a passport. You'll also need your ticket. If you're traveling with the kids, check with your airline about which documents they may need.
  • To keep you occupied on the short hop to Des Plaines, download some new tracks or restock the audiobook library on your smartphone. Food can also be a tasty distraction while in the air, so maybe even bring some light snacks.
  • No matter what the temperature is doing outside, plane cabins can get seriously cold. Bring a hoodie on board to keep yourself comfortable.

How many direct flights are there to Des Plaines?
Each month, there are 2,332 direct flights to Des Plaines. Select from an excellent range of airlines, including United Airlines, American Airlines and Delta Air Lines. Other carriers that jet to Des Plaines nonstop are Southwest Airlines, Spirit Airlines and Air Canada.
How do I get cheap first-class/business deals to Des Plaines?
There are ways of booking first or business-class fares to Des Plaines that won't burn a hole through your savings. Pick up a seat in the pointy end of the plane for less with these handy tips:

  • Be more flexible with your travel dates and wait for early bird or last-minute sales on first or business-class airfares.
  • Plenty of low-cost airlines these days have superb business or premium-class seating for a reasonable price.
  • Bid for an upgrade in online auctions or upgrade your seat through your flight loyalty scheme.

How to get into Des Plaines from the airport?
Zip into central Des Plaines with an O'Hare Intl. Airport (ORD) car rental. Thrifty Car Rental and Dollar are two leading agencies at O'Hare Intl. Airport (ORD). Throw your bags in the trunk, head 4 miles to the north and you'll be in the hustle and bustle of the city in next to no time. Plenty of travelers also use public transportation or taxis to travel into town. From there, you can still rent a ride to explore more of the region with one of our Des Plaines car rentals.
What is the best time to go to Des Plaines?
Anytime is a fantastic time to experience Des Plaines, though May, July and August are the liveliest months. As with most places in the Northern Hemisphere, summer kicks off June 20. If you'd like to spend your days in a short-sleeved top than a heavy winter jacket, this time of year may be ideal for you. Expect average daytime highs of 75 ºF and nightly lows around 65 ºF.
Travel tips for Des Plaines

  • Wear your most comfortable kicks and explore this city on foot. There are plenty of fantastic attractions to take in, such as Allstate Arena and Rivers Casino.
  • You'll also want to check out the sights a quick drive from Des Plaines's center. Set out for Wrigley Field and McCormick Place and see another side of this vibrant destination.
  • When you want to explore other parts of Chicago, arrange a car rental and follow the road signs to Calumet City. Harvey is another popular city with a great deal to do and see.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.