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$67+ Cheap flights from Iowa to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Iowa to Chicago

Cheapest flights from Iowa to Chicago
Explore the most affordable flight options available from Iowa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:28 pmCID - ORD
Nonstop1h 27mUnited Airlines
Wed 1/71:00 pmORD - CID
Nonstop1h 20mUnited Airlines
Deal found 12/17$203
This United Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:30 amCID - ORD
Nonstop1h 28mUnited Airlines
Thu 1/18:20 pmORD - CID
Nonstop1h 14mUnited Airlines
Deal found 12/17$209
This American Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:44 pmOMA - ORD
1 stop6h 35mAmerican Airlines
Wed 1/73:50 pmORD - OMA
Nonstop1h 51mAmerican Airlines
Deal found 12/17$214
This United Airlines deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:46 pmDSM - ORD
Nonstop1h 39mUnited Airlines
Thu 1/18:10 pmORD - DSM
Nonstop1h 30mUnited Airlines
Deal found 12/15$219
This American Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/238:00 amCID - ORD
Nonstop1h 21mAmerican Airlines
Sat 1/312:43 pmORD - CID
Nonstop1h 09mAmerican Airlines
Deal found 12/16$224
This United Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:00 amOMA - ORD
Nonstop1h 55mUnited Airlines
Wed 1/78:10 pmORD - OMA
Nonstop1h 48mUnited Airlines
Deal found 12/17$226
This United Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:00 amCID - ORD
Nonstop1h 28mUnited Airlines
Sat 12/278:20 pmORD - CID
Nonstop1h 14mUnited Airlines
Deal found 12/16$233
This United Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:00 amDSM - ORD
Nonstop1h 38mUnited Airlines
Fri 1/24:31 pmORD - DSM
Nonstop1h 34mUnited Airlines
Deal found 12/16$235
This Southwest deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:05 amOMA - MDW
Nonstop1h 25mSouthwest
Wed 1/712:10 pmMDW - OMA
1 stop6h 30mSouthwest
Deal found 12/17$236
This American Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/277:39 amCID - ORD
Nonstop1h 28mAmerican Airlines
Mon 12/299:14 pmORD - CID
Nonstop1h 23mAmerican Airlines
Deal found 12/16$239
This American Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:56 pmDSM - ORD
Nonstop1h 51mAmerican Airlines
Sun 1/46:40 amORD - DSM
Nonstop1h 35mAmerican Airlines
Deal found 12/16$249
This United Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:10 amMCW - ORD
Nonstop1h 30mUnited Airlines
Wed 1/74:49 pmORD - MCW
Nonstop1h 31mUnited Airlines
Deal found 12/17$252

Find flight deals from Iowa to Chicago

Keep the following information in mind while searching for Iowa to Chicago flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$133
(United Airlines)

One-way from

$67
(Southwest)

Popular in

December

Cheapest in

September

Average price

$290

Good round-trip deal

$68 or less

Good one-way deal

$29 or less
Provider with most accurate pricing for Des Moines-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Des Moines-Chicago (CHI) flights.
Search Deals
From Iowa to Chicago (CHI)
Search Deals
One-way flight from Iowa to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Iowa to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Iowa to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Iowa 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, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Iowa to Chicago that are best for you.

Fly from

Iowa

Fly to

Chicago

Route

Depart

Return

Price

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Wed 1/7

8:00 am-9:55 am

Nonstop1h 55m

Chicago O'Hare Intl

Wed 1/7

8:10 pm-9:58 pm

Nonstop1h 48m

$133

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Wed 1/7

6:16 pm-8:05 pm

Nonstop1h 49m

Chicago O'Hare Intl

Wed 1/14

3:50 pm-5:41 pm

Nonstop1h 51m

$133

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Wed 1/14

6:05 am-1:08 pm

1 stop7h 03m

Chicago O'Hare Intl

Wed 1/21

6:45 pm-10:54 pm

1 stop4h 09m

$157

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Wed 1/7

10:34 am-5:26 pm

1 stop6h 52m

Chicago O'Hare Intl

Wed 1/14

6:15 am-11:36 am

1 stop5h 21m

$157

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Wed 1/7

6:05 am-1:08 pm

1 stop7h 03m

Chicago O'Hare Intl

Wed 1/7

6:45 pm-10:54 pm

1 stop4h 09m

$157

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 1/7

1:50 pm-7:55 pm

1 stop6h 05m

Chicago Midway

Sat 1/10

8:20 am-10:00 am

Nonstop1h 40m

$162

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Wed 2/18

3:10 pm-4:35 pm

Nonstop1h 25m

Chicago Midway

Sat 2/21

2:05 pm-12:05 am

2 stops10h 00m

$167

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Thu 1/15

8:00 am-9:55 am

Nonstop1h 55m

Chicago O'Hare Intl

Thu 1/22

3:55 pm-5:36 pm

Nonstop1h 41m

$171

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Wed 1/7

10:34 am-5:26 pm

1 stop6h 52m

Chicago O'Hare Intl

Sat 1/10

11:05 am-5:24 pm

1 stop6h 19m

$174

Cedar RapidsChicago

CID - ORD

CIDORD

Cedar Rapids

Fri 1/16

10:05 am-11:37 am

Nonstop1h 32m

Chicago O'Hare Intl

Tue 1/20

8:00 am-9:24 am

Nonstop1h 24m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 60 results
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Best time to book a flight from Iowa to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Iowa with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Iowa to Chicago

What is the cheapest month to book a flight from Iowa to Chicago?

Currently, April is the cheapest month in which you can book a flight from Iowa to Chicago (average of $58). Flying from Iowa to Chicago in July is currently the most expensive (average of $188). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from IA to CHI?

Find hourly flight availability from Iowa to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 45% on flights from Iowa to Chicago by exploring options for tickets in the morning.

What is the cheapest day to fly from Iowa to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Iowa to Chicago. Price data was last updated on December 13, 2025.

Travelers seeking maximum savings on their Iowa to Chicago flight should consider departing on Thursday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Iowa to Chicago

Explore weekly flight availability from Iowa to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 18, 2025.

The most flights from USIA to CHI are scheduled on a Thursday (42 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (5 on average).

Related info for your journey

Find useful and relevant information for your journey from Iowa to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Iowa to Chicago?

    A quick flight from Iowa to Chicago can take about 1h 49m. United Airlines provides one of the quickest options available for as low as $133. There are 415 mi between Iowa and Chicago. This flight may include one or multiple stops.

  • What are the most popular routes from Iowa to Chicago?

    Most travelers choose Omaha Eppley Airfield - Chicago O'Hare Intl, Des Moines - Chicago O'Hare Intl or Cedar Rapids - Chicago O'Hare Intl when deciding on the best route from Iowa to Chicago.

  • What are the most reliable airlines from Iowa to Chicago?

    Before booking your flight to Chicago from Iowa, check out the most reliable airlines to get you to your destination on time: Envoy Air (88%), Copa Airlines (82%), Avianca( 73%).

  • What are the cheapest flights from Iowa to Chicago?

    Looking for the cheapest flight from Iowa to Chicago? While on average our users pay $1,184, our data indicates the cheapest price to be $167. The most popular route (Omaha Eppley Airfield - Chicago O'Hare Intl), is priced around $133.

  • Can I find deals for flights from Iowa to Chicago that include hotel bookings?

    Yes. In addition to deals on Iowa to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Iowa to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Iowa to Chicago.

  • Can I find deals for business class flights from Iowa to Chicago?

    Yes. Cheapflights offers flight deals from Iowa to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Iowa to Chicago?

    Currently, April is the cheapest month in which you can book a flight from Iowa to Chicago (average of $58). Flying from Iowa to Chicago in July is currently the most expensive (average of $188). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Iowa to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Iowa to Chicago

Discover the top 4 airlines that operate flights from Iowa to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Southern / MokuleleCheapest$83Average$103FlexibilityNo cancel feeOn-timeN/A
Denver Air ConnectionCheapest$129Average$173FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$179Average$308FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$265FlexibilityNo cancel feeOn-time69%

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