DSM - CHI

$113 Find Cheap Flights from Des Moines to Chicago - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$211
Typical prices: $267-$442
Frontier
Mon 12/3Mon 12/10
DSM - ORD • 1 stop
Cheapest non-stop
$236
Typical prices: $265-$444
United Airlines
Sat 11/17Sun 11/18
DSM - ORD • Non-stop
Nonstop flights
You can fly direct with United Airlines, American Airlines and Southwest. Average duration is 1h 40m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 12 weeks in advance save around 60% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 34% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $326 (round-trip)
Shortest trip • 6h 30m (one-way)
Insights
Insights
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Booking Insights
Expert advice
Flight Deals

Cheap Flights from Des Moines to Chicago (DSM-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Des Moines to Chicago

Thu, Dec 3 - Thu, Dec 10
Frontier Logo
8:35 pm - 12:53 amDSM  Des Moines-ORD Chicago O'Hare Intl
28h 18m1 stop Denver Intl
Frontier Logo
7:25 am - 7:42 pmORD  Chicago O'Hare Intl-DSM Des Moines
12h 17m1 stop Denver Intl
$211Frontier
Tue, Nov 17 - Wed, Nov 18
United Airlines Logo
8:00 am - 9:40 amDSM  Des Moines-ORD Chicago O'Hare Intl
1h 40mnonstop
United Airlines Logo
8:25 pm - 9:55 pmORD  Chicago O'Hare Intl-DSM Des Moines
1h 30mnonstop
$236United Airlines
Wed, Nov 25 - Fri, Nov 27
American Airlines Logo
7:25 pm - 9:15 pmDSM  Des Moines-ORD Chicago O'Hare Intl
1h 50mnonstop
American Airlines Logo
5:18 pm - 6:54 pmORD  Chicago O'Hare Intl-DSM Des Moines
1h 36mnonstop
$237American Airlines
Tue, Dec 1 - Fri, Dec 18
American Airlines Logo
7:24 pm - 9:14 pmDSM  Des Moines-ORD Chicago O'Hare Intl
1h 50mnonstop
American Airlines Logo
7:35 am - 9:12 amORD  Chicago O'Hare Intl-DSM Des Moines
1h 37mnonstop
$237American Airlines
Tue, Dec 15 - Tue, Dec 22
Southwest Logo
6:00 am - 7:25 amDSM  Des Moines-MDW Chicago Midway
1h 25mnonstop
Southwest Logo
9:55 am - 11:15 amMDW  Chicago Midway-DSM Des Moines
1h 20mnonstop
$237Southwest
Fri, Dec 18 - Fri, Dec 25
Southwest Logo
7:15 pm - 8:35 pmDSM  Des Moines-MDW Chicago Midway
1h 20mnonstop
Southwest Logo
10:05 am - 11:25 amMDW  Chicago Midway-DSM Des Moines
1h 20mnonstop
$237Southwest
Wed, Dec 2 - Wed, Dec 9
United Airlines Logo
6:15 am - 7:57 amDSM  Des Moines-ORD Chicago O'Hare Intl
1h 42mnonstop
United Airlines Logo
3:40 pm - 5:14 pmORD  Chicago O'Hare Intl-DSM Des Moines
1h 34mnonstop
$237United Airlines
Thu, Dec 3 - Mon, Dec 7
United Airlines Logo
3:20 pm - 5:00 pmDSM  Des Moines-ORD Chicago O'Hare Intl
1h 40mnonstop
United Airlines Logo
8:55 am - 10:37 amORD  Chicago O'Hare Intl-DSM Des Moines
1h 42mnonstop
$237United Airlines
Thu, Dec 3 - Sun, Dec 6
Frontier Logo
8:35 pm - 12:53 amDSM  Des Moines-ORD Chicago O'Hare Intl
28h 18m1 stop Denver Intl
Frontier Logo
7:00 am - 7:50 pmORD  Chicago O'Hare Intl-DSM Des Moines
12h 50m1 stop Denver Intl
$244Frontier
Thu, Dec 17 - Sun, Dec 20
Frontier Logo
8:26 pm - 12:26 amDSM  Des Moines-ORD Chicago O'Hare Intl
28h 00m1 stop Denver Intl
Frontier Logo
7:45 am - 7:31 pmORD  Chicago O'Hare Intl-DSM Des Moines
11h 46m1 stop Denver Intl
$244Frontier
Booking Insights

Price, demand and travel trends for Des Moines to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Des Moines to Chicago?

Round-trip flights from Des Moines to Chicago typically range from $267 to $442. The lowest price found in the past 5 days was $211, on Frontier.

What is the cheapest Des Moines to Chicago flight route?

There's little price difference between Des Moines to Chicago routes. They average around $339 round-trip, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Des Moines to Chicago?

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Des Moines to Chicago. It’s 8% cheaper than the average day, while Monday is the most expensive, with prices 14% higher.

What’s the cheapest month to fly from Des Moines to Chicago?

•February is the cheapest month to fly from Des Moines to Chicago at $224 round-trip.
•July ($423) and April ($394) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 88% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Des Moines to Chicago the cheapest?

Flights from Des Moines to Chicago are cheapest 12 weeks before departure. Booking in this window typically costs about 60% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Des Moines to Chicago

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Jessica Macdonald

Jessica Macdonald

Expert on Lufthansa

Currently based in Scotland after living in South Africa and the United States, Jessica has been writing travel and aviation content for more than 10 years. She regularly contributes to Travel + Leisure and TripSavvy, and has had work published by Condé Nast Traveller and The Independent. She has traveled to more than 50 countries across six continents.

Duncan Madden

Duncan Madden

Expert on British Airways

Duncan is a freelance travel writer, copywriter and book author in constant search of travel stories and the perpetual sensation of being on holiday. He’s never happier than when on a dusty trail in search of empty waves or ducking under the piste tape in search of snowbound solitude. British born, living in Germany, but happiest heading for the horizon. His first book, Found in Translation, explores the etymologies and stories of country names around the world and is out now.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Key details for Des Moines to Chicago flights

Low season

April

Cheapest flight

$113
Beat the crowds with an average 21% drop in travelers.
The most popular month to fly with an average 18% increase in travelers.
One-way flight from Des Moines to Chicago O'Hare Intl Airport

When to book flights from Des Moines to Chicago

Are your dates flexible? Find out the best times to travel from Des Moines to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Des Moines to Chicago flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Des Moines to Chicago?

    These are the earliest and latest flight times available from Des Moines to Chicago:

    • Earliest: departs at 5:00 am and lands at 6:40 am
    • Latest: departs at 9:00 pm and lands at 10:40 pm.

    The flight takes about 1h 40m.

  • What cabin classes can I book on flights from Des Moines to Chicago?

    Three cabin classes are available on flights from Des Moines to Chicago:

    • Economy Class
    • Business Class
    • First Class

  • How long is a flight from Des Moines to Chicago?

    A nonstop flight from Des Moines to Chicago takes 1h 40m, covering 312 miles.

  • Do I need a passport to fly from Des Moines to Chicago?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Des Moines to Chicago flight?

    Round-trip flights from Des Moines to Chicago range from $267 to $442, with an average of $339 over the past 12 months. Anything below $267 counts as a good deal.

  • How expensive are last-minute Des Moines to Chicago flights?

    Last-minute fares on this route (booked within two weeks of departure) run 41% above the $339 route average. Book 12 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Des Moines to Chicago?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $326 round-trip via Fort Lauderdale (FLL), compared to $340 for nonstop.

  • What is the standard checked-bag allowance on flights from Des Moines to Chicago?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • How are flight departures from Des Moines to Chicago spread across the day?

    Morning is the busiest departure period on Des Moines to Chicago flights, with 59% of flights leaving in that window. Afternoon departures account for 25%, evening flights for 16%, and night flights for 0%.

  • Have flight prices from Des Moines to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $211 to $1,896. That means the highest observed fare was about 9x higher than the lowest one.

  • Which airlines offer Wi-Fi on Des Moines to Chicago flights?

    American Airlines is the only airline on the Des Moines to Chicago route offering in-flight Wi-Fi. Pricing depends on fare class.

  • How are flight prices from Des Moines to Chicago looking right now?

    One-way fares from Des Moines to Chicago are currently lower than usual. Average one-way flight prices are about $120, which is 49% below the typical average for this route.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates averaging $63:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

    Near Chicago Midway Airport (MDW) — daily rates averaging $86:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

  • Which airports can I use when flying from Des Moines to Chicago?

    Flights from Des Moines to Chicago usually depart from Des Moines (DSM) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airports do connecting flights from Des Moines to Chicago pass through?

    Connecting flights from Des Moines to Chicago most commonly pass through:

    • Detroit Metropolitan Wayne County (DTW) - 50% of one-stop connections
    • Fort Lauderdale (FLL) - 50% of one-stop connections

  • Can I save money by using flexible dates for flights from Des Moines to Chicago?

    Yes. Flexible dates can save you up to 19% on flights from Des Moines to Chicago. Tuesday is the cheapest departure day at $315 round-trip on average, while Monday is the most expensive at $388, a difference of $73.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Des Moines to Chicago?

    3 airlines operate flights between Des Moines and Chicago. The airlines offering nonstop flights on this route include:

    • United Airlines
    • American Airlines
    • Southwest

  • How much time can I save by choosing a different layover airport from Des Moines to Chicago?

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 6h 30m, compared with 14h 48m via Fort Lauderdale (FLL).

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Des Moines to Chicago flights?

    Among airlines operating Des Moines to Chicago flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Des Moines to Chicago flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class
    • Southwest: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

  • What are the transport options from Chicago Midway International Airport?

    From MDW to downtown Chicago and other nearby cities or locations, travelers can choose between trains, shuttle buses, taxis, rideshare apps, car rental services, or free hotel shuttles to their booked hotel. From MDW to downtown Chicago the CTA train charges around $3, taxis charge around $25, Uber and Lyft charge around $30, and car rental companies charge around $36 per day for their rentals.

  • Does Chicago Midway International Airport have accessible services?

    At MDW passengers and visitors who have special needs are catered for by special facilities. The elevators, restrooms, diaper changing facilities, and telephones have amenities that are accessible for wheelchair users and people with disabilities. MDW provides numerous handicap parking spaces, and wheelchair assistance, the bus stations have special elevators for wheelchair users and there are accessible taxis that operate from the airport.

  • Which is the best airline alliance to use for flights from Des Moines to Chicago?

    Both Oneworld Alliance and Star alliance operate in DSM and MDW. Oneworld Alliance serves over 14 airlines, 1000 destinations, and over 650 lounges while Star Alliance serves over 27 airlines, over 1300 destinations, and has over 1000 lounges. Star Alliance only offers two tiers of elite status and operates in America while Oneworld offers three tiers and operates in both America and Alaska, making the latter better.

  • What cities are near Chicago Midway International Airport?

    Chicago Midway International Airport in Illinois is near cities like Burbank, Cicero, Justice, Lyons, Summit, Berwyn, and Evergreen Park.

Your guide to booking Des Moines to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Tuesday departure and avoid flying on Monday. On this route, Tuesday flights average $315, about $73 less than Monday fares (19% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 12 weeks before you fly. On this route, that window historically saves about 60% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Des Moines to Chicago trip for February. Fares historically average $224 round-trip in that month - typically $199 less than the most expensive month, which is July (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Fort Lauderdale Airport (FLL) can be cheaper than flying direct. The cheapest layover option averages $326 round-trip on this route - about $14 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport
  • Des Moines International Airport (DSM) is a mid-sized commercial service airport in Iowa served by six airlines that offer non-stop flights to over 20 destinations worldwide. It has one main terminal and two concourses, Concourses A and C. The DSM Airport shuttle that transports visitors of DSM between the terminal and the parking lots is free.
  • On arrival at Chicago Midway International (MDW) and in need of luggage services, worry not. MDW provides free baggage carts for rent for this very purpose. You can find them at the entrances and exits of the Baggage Claim area.
  • At DSM, travelers with infants can access a private Mamava Nursing Pod sponsored by Unity Point Health to breastfeed, pump, or for diaper changing. The pod is located immediately after the TSA Security Checkpoint across the DSM Police Desk. DSM also has family rooms that can be used as an alternative to the nursing pod within the terminal.
  • Travelers at DSM are waiting for their flight and need to catch up with their work and can access the Business Center free of charge. There you can use the workstations and the free internet access provided courtesy of DSM. It’s located at Level A2 of Concourse A.
  • DSM provides both long-term and short-term parking at affordable rates for customers and visitors. Short-term parking is free for the first 20 minutes and after that, it costs around $1 for every 20 minutes to a daily maximum of around $36. On the other hand, general long-term parking charges around $2 per hour to a daily maximum of around $15 while premium long-term parking costs around $1 per 20 minutes to a daily maximum of around $25.

Prefer to fly direct from Des Moines to Chicago?

 
Find which airlines fly direct from Des Moines Airport to Chicago, which days they fly and book direct flights.

Direct departures

Des Moines to Chicago

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

Chicago to Des Moines

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

More options for your flight from Des Moines to Chicago

Complete your trip to Chicago with a hotel stay or car rental