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Cheap flights from Des Moines to Chicago from $65

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Des Moines to Chicago departing on 11/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Frontier Logo
2:32 pm - 12:16 amDSM-ORD
9h 44m1 stop
Frontier Logo
5:00 am - 12:47 pmORD-DSM
7h 47m1 stop
$189Frontier
Find Deal
Fri, Oct 31 - Sun, Nov 2
American Airlines Logo
6:07 pm - 7:50 pmDSM-ORD
1h 43mnonstop
American Airlines Logo
7:02 am - 8:34 amORD-DSM
1h 32mnonstop
$190American Airlines
Find Deal
Mon, Oct 27 - Mon, Nov 3
American Airlines Logo
10:16 am - 11:49 amDSM-ORD
1h 33mnonstop
American Airlines Logo
6:55 am - 8:22 amORD-DSM
1h 27mnonstop
$194American Airlines
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Wed, Oct 1 - Thu, Oct 16
Southwest Logo
4:45 pm - 10:05 pmDSM-MDW
5h 20m1 stop
Southwest Logo
7:40 am - 11:00 amMDW-DSM
3h 20m1 stop
$196Southwest
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Tue, Oct 14 - Thu, Oct 16
Delta Logo
11:06 am - 5:43 pmDSM-MDW
6h 37m1 stop
Delta Logo
9:20 am - 1:59 pmMDW-DSM
4h 39m1 stop
$197Delta
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Tue, Oct 28 - Tue, Nov 4
Delta Logo
10:00 am - 4:11 pmDSM-ORD
6h 11m1 stop
Delta Logo
1:25 pm - 8:35 pmORD-DSM
7h 10m1 stop
$197Delta
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Tue, Oct 28 - Tue, Nov 4
Southwest Logo
3:50 pm - 7:05 pmDSM-MDW
3h 15m1 stop
Southwest Logo
6:50 am - 11:25 amMDW-DSM
4h 35m1 stop
$209Southwest
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Sat, Oct 4 - Sun, Oct 5
United Airlines Logo
3:25 pm - 4:58 pmDSM-ORD
1h 33mnonstop
United Airlines Logo
1:03 pm - 2:23 pmORD-DSM
1h 20mnonstop
$224United Airlines
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Fri, Sep 26 - Sun, Sep 28
Logo
2:37 pm - 11:53 pmDSM-ORD
9h 16m1 stop
Logo
7:43 pm - 2:50 pmORD-DSM
19h 07m2 stops
$226
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Thu, Oct 23 - Thu, Oct 30
Logo
10:14 am - 10:31 amDSM-ORD
24h 17m2 stops
Logo
12:53 pm - 1:32 pmORD-DSM
24h 39m1 stop
$245
Find Deal
Wed, Sep 24 - Thu, Sep 25

Frontier flights from Des Moines to Chicago

Our best Frontier deals on Des Moines to Chicago flight tickets
Frontier
Oct 31
DSM2:32 pmDes Moines
9h 44m
1 stop
ORD12:16 amChicago O'Hare Intl
Nov 2
ORD5:00 amChicago O'Hare Intl
7h 47m
1 stop
DSM12:47 pmDes Moines
$189
Find similar
Frontier
Sep 26
DSM2:25 pmDes Moines
9h 34m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 28
ORD6:00 amChicago O'Hare Intl
7h 40m
1 stop
DSM1:40 pmDes Moines
$207
Find similar
Frontier
Oct 23
DSM2:37 pmDes Moines
9h 59m
1 stop
MDW12:36 amChicago Midway
Oct 30
MDW9:43 pmChicago Midway
16h 04m
2 stops
DSM1:47 pmDes Moines
$221
Find similar

American Airlines flights from Des Moines to Chicago

Our best American Airlines deals on Des Moines to Chicago flight tickets
American Airlines
Oct 27
DSM6:07 pmDes Moines
1h 43m
ORD7:50 pmChicago O'Hare Intl
Nov 3
ORD7:02 amChicago O'Hare Intl
1h 32m
DSM8:34 amDes Moines
$190
Find similar
American Airlines
Sep 26
DSM5:00 amDes Moines
1h 28m
ORD6:28 amChicago O'Hare Intl
Nov 12
ORD1:58 pmChicago O'Hare Intl
1h 34m
DSM3:32 pmDes Moines
$194
Find similar
American Airlines
Sep 26
DSM8:55 amDes Moines
1h 33m
ORD10:28 amChicago O'Hare Intl
Sep 29
ORD10:06 pmChicago O'Hare Intl
1h 22m
DSM11:28 pmDes Moines
$199
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Des Moines to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 14, 2025.
Use the filters below to find and compare flights from Des Moines to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Fri 10/31

2:32 pm-12:16 am

1 stop9h 44m

Chicago O'Hare Intl

Sun 11/2

5:00 am-12:47 pm

1 stop7h 47m

$189

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Mon 10/27

6:07 pm-7:50 pm

Nonstop1h 43m

Chicago O'Hare Intl

Mon 11/3

7:02 am-8:34 am

Nonstop1h 32m

$190

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Wed 10/1

10:16 am-11:49 am

Nonstop1h 33m

Chicago O'Hare Intl

Thu 10/16

6:55 am-8:22 am

Nonstop1h 27m

$194

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 10/14

4:45 pm-10:05 pm

1 stop5h 20m

Chicago Midway

Thu 10/16

7:40 am-11:00 am

1 stop3h 20m

$196

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 10/28

11:06 am-5:43 pm

1 stop6h 37m

Chicago Midway

Tue 11/4

9:20 am-1:59 pm

1 stop4h 39m

$197

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Tue 10/28

10:00 am-4:11 pm

1 stop6h 11m

Chicago O'Hare Intl

Tue 11/4

1:25 pm-8:35 pm

1 stop7h 10m

$197

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 10/4

3:50 pm-7:05 pm

1 stop3h 15m

Chicago Midway

Sun 10/5

6:50 am-11:25 am

1 stop4h 35m

$209

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Fri 9/26

3:25 pm-4:58 pm

Nonstop1h 33m

Chicago O'Hare Intl

Sun 9/28

1:03 pm-2:23 pm

Nonstop1h 20m

$224

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Thu 10/23

2:37 pm-11:53 pm

1 stop9h 16m

Chicago O'Hare Intl

Thu 10/30

7:43 pm-2:50 pm

2 stops19h 07m

$226

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Wed 9/24

10:14 am-10:31 am

2 stops24h 17m

Chicago O'Hare Intl

Thu 9/25

12:53 pm-1:32 pm

1 stop24h 39m

$245

Flights are sorted by cheapest round-trip flights first.

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See travel insights to Chicago from

How to get the cheapest flight ticket from Des Moines to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Des Moines, with most prices found around $224. If you’re not able to fly to Chicago in May, then September is your next best option. Flight prices from Des Moines to Chicago during September average around $224.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $569. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Des Moines to Chicago for around $870.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Des Moines to Chicago during this time can be as low as $249. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $1,093.

What is the cheapest Des Moines to Chicago flight route?

Fly from Des Moines to Chicago O'Hare Intl for the best Des Moines - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Des Moines when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $253 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Des Moines for as low as $196 on momondo.

What cabin class options are available on Des Moines to Chicago flights?

There are 4 cabin classes available to choose from on Des Moines to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Des Moines to Chicago flights?

You could potentially save up to 58% on your flight if you consider stops on a Des Moines to Chicago flight.

How have Des Moines to Chicago flight prices changed over time?

As of September 2025, prices for Des Moines to Chicago flights are approximately 133% more expensive when compared to flights at the same time last year.

When to book flights from Des Moines to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Des Moines to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Des Moines to Chicago (DSM to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Des Moines to Chicago

Best Price Found

$220

Fastest flight time

1h 20m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Des Moines in the past 72 hours is $220. The best round-trip flight deal from Des Moines to Chicago found on momondo in the last 72 hours is $346.
The fastest flight from Des Moines to Chicago takes 1h 20m
Direct flights go from Des Moines to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • How far is Des Moines to Chicago by plane?

    Chicago is 309.8 mi away from Des Moines. By plane, this route typically takes 1h 31m.

  • When did momondo last update prices for flights from Des Moines Airport to Chicago?

    Prices for flights from Des Moines Airport to Chicago were last updated today.

  • How many operators does momondo search for flights from Des Moines Airport to Chicago?

  • How old do you have to be to fly from Des Moines Airport to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Des Moines Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Des Moines to Chicago?

  • What is the most popular airline from Des Moines to Chicago?

Best airlines flying from Des Moines to Chicago

Compare and see reviews for airlines that fly from Des Moines to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $189Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $189Free CancellationRating
7.4
8,931 reviews
Search United Airlines flights

  • United Airlines Flights From Des Moines to Chicago

    United Airlines operates around 28 flights from Des Moines to Chicago every week. The average price of these flights found in the last 72 hours has been $254, but momondo users have found United Airlines deals from Des Moines to Chicago from as low as $189 round-trip. United Airlines has been scored 7.4/10 in 8,931 reviews.

  • American Airlines Flights From Des Moines to Chicago

    The best American Airlines deal for Des Moines to Chicago flight tickets found on momondo in the last 72 hours was $189, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at $240 round-trip. American Airlines operates 23 flights out of Des Moines into Chicago in an average week, so prices vary by time and availability. 10,000 American Airlines reviews by users on momondo have scored the airline at 7.2/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Des Moines to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Des Moines.

Can I find flights from Des Moines to Chicago with flexible booking policies on momondo?

All flight searches from Des Moines to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Des Moines to Chicago?

Once all potential Des Moines to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Des Moines to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Des Moines are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport