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$43+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — CHI
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
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 February 5, 2026.

This Mytrip deal was found by Cheapflights users on 2/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/199:00 am
BRL
-
ORD
Nonstop1h 10m
Contour
Mon 2/2310:50 am
ORD
-
BRL
Nonstop1h 20m
Contour
Deal found 2/3$85
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/179:00 am
BRL
-
ORD
Nonstop1h 10m
Contour
Sat 2/2110:50 am
ORD
-
BRL
Nonstop1h 20m
Contour
Deal found 2/2$86
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/204:20 pm
BRL
-
ORD
Nonstop1h 25m
Contour
Sun 3/226:25 pm
ORD
-
BRL
Nonstop1h 20m
Contour
Deal found 2/2$87
This Mytrip deal was found by Cheapflights users on 2/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/119:00 am
BRL
-
ORD
Nonstop1h 10m
Contour
Wed 2/1810:50 am
ORD
-
BRL
Nonstop1h 20m
Contour
Deal found 2/4$93
This Contour deal was found by Cheapflights users on 2/2. 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 Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/164:25 pm
BRL
-
ORD
Nonstop1h 20m
Contour
Wed 2/2510:50 am
ORD
-
BRL
Nonstop1h 20m
Contour
Deal found 2/2$100
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/64:25 pm
BRL
-
ORD
Nonstop1h 20m
Contour
Sun 2/810:50 am
ORD
-
BRL
Nonstop1h 20m
Contour
Deal found 2/2$105
This Contour deal was found by Cheapflights users on 2/4. 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 Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/134:25 pm
BRL
-
ORD
Nonstop1h 20m
Contour
Sun 2/1510:50 am
ORD
-
BRL
Nonstop1h 20m
Contour
Deal found 2/4$134
This Frontier deal was found by Cheapflights users on 2/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1911:32 am
OMA
-
ORD
1 stop11h 42m
Frontier
Mon 2/235:05 am
ORD
-
OMA
1 stop7h 59m
Frontier
Deal found 2/4$160
This Southwest deal was found by Cheapflights users on 2/3. 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.
Tue 4/143:15 pm
DSM
-
MDW
Nonstop1h 20m
Southwest
Thu 4/169:45 pm
MDW
-
DSM
Nonstop1h 20m
Southwest
Deal found 2/3$164
This American Airlines deal was found by Cheapflights users on 2/3. 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 4/16:40 am
DSM
-
ORD
Nonstop1h 45m
American Airlines
Sat 4/44:54 pm
ORD
-
DSM
Nonstop1h 25m
American Airlines
Deal found 2/3$164
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Fri 4/176:37 pm
LSE
-
ORD
Nonstop1h 35m
American Airlines
Wed 4/224:41 pm
ORD
-
LSE
Nonstop1h 26m
American Airlines
Deal found 2/3$169
This Southwest deal was found by Cheapflights users on 2/4. 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.
Thu 4/95:25 am
DSM
-
MDW
Nonstop1h 20m
Southwest
Mon 4/1310:20 am
MDW
-
DSM
Nonstop1h 25m
Southwest
Deal found 2/4$171

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 February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$85
(Mytrip)

One-way from

$43
(Booking.com)

Popular in

January

Cheapest in

September

Average price

$260

Good round-trip deal

$218 or less

Good one-way deal

$188 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. 9% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 5, 2026.
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

BurlingtonChicago

BRL - ORD

BRLORD

Burlington

Wed 4/29

9:10 am-10:35 am

Nonstop1h 25m

Chicago O'Hare Intl

Sat 5/2

12:00 pm-1:20 pm

Nonstop1h 20m

$85

BurlingtonChicago

BRL - ORD

BRLORD

Burlington

Fri 2/20

4:25 pm-5:45 pm

Nonstop1h 20m

Chicago O'Hare Intl

Tue 2/24

10:50 am-12:10 pm

Nonstop1h 20m

$85

BurlingtonChicago

BRL - ORD

BRLORD

Burlington

Mon 3/2

8:45 am-10:10 am

Nonstop1h 25m

Chicago O'Hare Intl

Mon 3/9

6:25 pm-7:45 pm

Nonstop1h 20m

$85

BurlingtonChicago

BRL - ORD

BRLORD

Burlington

Thu 2/19

9:00 am-10:10 am

Nonstop1h 10m

Chicago O'Hare Intl

Mon 2/23

10:50 am-12:10 pm

Nonstop1h 20m

$85

BurlingtonChicago

BRL - ORD

BRLORD

Burlington

Tue 2/17

9:00 am-10:10 am

Nonstop1h 10m

Chicago O'Hare Intl

Sat 2/21

10:50 am-12:10 pm

Nonstop1h 20m

$86

BurlingtonChicago

BRL - ORD

BRLORD

Burlington

Fri 3/20

4:20 pm-5:45 pm

Nonstop1h 25m

Chicago O'Hare Intl

Sun 3/22

6:25 pm-7:45 pm

Nonstop1h 20m

$87

BurlingtonChicago

BRL - ORD

BRLORD

Burlington

Wed 2/11

9:00 am-10:10 am

Nonstop1h 10m

Chicago O'Hare Intl

Wed 2/18

10:50 am-12:10 pm

Nonstop1h 20m

$93

BurlingtonChicago

BRL - ORD

BRLORD

Burlington

Fri 2/20

9:00 am-10:10 am

Nonstop1h 10m

Chicago O'Hare Intl

Sun 2/22

10:50 am-12:10 pm

Nonstop1h 20m

$100

BurlingtonChicago

BRL - ORD

BRLORD

Burlington

Mon 2/16

9:00 am-10:10 am

Nonstop1h 10m

Chicago O'Hare Intl

Wed 2/25

10:50 am-12:10 pm

Nonstop1h 20m

$100

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 4/14

3:15 pm-4:35 pm

Nonstop1h 20m

Chicago Midway

Thu 4/16

9:45 pm-11:05 pm

Nonstop1h 20m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

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 $60). Flying from Iowa to Chicago in July is currently the most expensive (average of $187). 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 February 5, 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 26% 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 January 31, 2026.

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. Saturday 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 February 5, 2026.

The most flights from USIA to CHI are scheduled on a Thursday (37 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 on average).

How much does it cost to fly round-trip from Iowa to Chicago?

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 20m. Contour provides one of the quickest options available for as low as $164. There are 305 mi between Iowa and Chicago. All flights are typically nonstop.

  • What are the cheapest airlines to fly from Iowa to Chicago one-way?

    The cheapest airlines for a one-way flight from Iowa to Chicago are Etihad Airways ($402), Turkish Airlines ($617), and Emirates ($667).

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

    Most travelers choose Omaha Eppley Airfield - Chicago O'Hare Intl, Omaha Eppley Airfield - Chicago Midway or Des Moines - 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: Lufthansa (77%), ANA (73%), Copa Airlines( 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 $1,099, our data indicates the cheapest price to be $107. The most popular route (Omaha Eppley Airfield - Chicago O'Hare Intl), is priced around $217.

  • 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 $60). Flying from Iowa to Chicago in July is currently the most expensive (average of $187). 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 5 airlines flying from Iowa to Chicago

Discover the top 5 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 February 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
Southern / MokuleleCheapest$44Average$103FlexibilityNo cancel feeOn-timeN/A
ContourCheapest$59Average$88FlexibilityNo cancel feeOn-timeN/A
Denver Air ConnectionCheapest$129Average$202FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$148Average$312FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$280FlexibilityNo cancel feeOn-time69%

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