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$55+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap 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 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$132
(Booking.com)

One-way from

$55
(Frontier)

Popular in

June

Cheapest in

November

Average price

$295

Good round-trip deal

$130 or less

Good one-way deal

$64 or less
Provider with most accurate pricing for Des Moines-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Des Moines-Chicago (CHI) flights.
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From Iowa to Chicago (CHI)
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One-way flight from Iowa to Chicago (CHI)
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Highest demand for flights based on searches. 10% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Iowa to Chicago (CHI).
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Price to beat on a one-way flight from Iowa to Chicago (CHI).
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Find 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 20, 2025.

This Denver Air Connection deal was found by Cheapflights users on 2/20. 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 Denver Air Connection is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/83:55 pmDBQ - ORD
Nonstop0h 55mDenver Air Connection
Sun 4/132:30 pmORD - DBQ
Nonstop0h 55mDenver Air Connection
Deal found 2/20$138
This Mytrip deal was found by Cheapflights users on 2/19. 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 4/48:17 pmDSM - ORD
1 stop17h 03mFrontier
Fri 4/116:40 amORD - DSM
1 stop12h 37mFrontier
Deal found 2/19$169
This American Airlines deal was found by Cheapflights users on 2/19. 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 7/2611:26 amMLI - ORD
Nonstop1h 09mAmerican Airlines
Sat 8/210:00 pmORD - MLI
Nonstop0h 58mAmerican Airlines
Deal found 2/19$179
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/285:45 amDSM - ORD
Nonstop1h 22mAmerican Airlines
Sun 3/3012:57 pmORD - DSM
Nonstop1h 25mAmerican Airlines
Deal found 2/20$189
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Fri 3/73:50 pmMLI - ORD
Nonstop1h 07mUnited Airlines
Tue 3/119:05 amORD - MLI
Nonstop1h 14mUnited Airlines
Deal found 2/20$190
This United Airlines deal was found by Cheapflights users on 2/20. 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 4/1410:03 amSUX - ORD
Nonstop1h 39mUnited Airlines
Mon 4/288:40 pmORD - SUX
Nonstop1h 46mUnited Airlines
Deal found 2/20$194
This Southwest deal was found by Cheapflights users on 2/20. 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 3/258:25 amOMA - MDW
2 stops9h 40mSouthwest
Wed 3/261:50 pmMDW - OMA
2 stops8h 40mSouthwest
Deal found 2/20$207
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/215:49 pmOMA - ORD
Nonstop1h 36mAmerican Airlines
Fri 3/288:30 amORD - OMA
Nonstop1h 44mAmerican Airlines
Deal found 2/20$207
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/311:31 pmDSM - MDW
1 stop4h 32mDelta
Sat 9/69:20 amMDW - DSM
1 stop4h 44mDelta
Deal found 2/20$209
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2612:30 pmDSM - ORD
1 stop3h 41mDelta
Wed 4/306:35 amORD - DSM
1 stop4h 44mDelta
Deal found 2/20$209
This United Airlines deal was found by Cheapflights users on 2/20. 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 10/18:00 amDSM - ORD
Nonstop1h 30mUnited Airlines
Sun 10/57:35 pmORD - DSM
Nonstop1h 16mUnited Airlines
Deal found 2/20$211
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/811:18 amOMA - MDW
1 stop6h 25mDelta
Tue 3/1110:25 amMDW - OMA
1 stop6h 07mDelta
Deal found 2/20$212

Find flights from Iowa to Chicago within your budget

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 20, 2025.

Fly from

Iowa

Fly to

Chicago

Route

Depart

Return

Price

DubuqueChicago

DBQ - ORD

DBQORD

Dubuque

Fri 4/11

3:55 pm-4:50 pm

Nonstop0h 55m

Chicago O'Hare Intl

Sun 4/13

2:30 pm-3:25 pm

Nonstop0h 55m

$132

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Fri 4/4

8:17 pm-1:20 pm

1 stop17h 03m

Chicago O'Hare Intl

Fri 4/11

6:40 am-7:17 pm

1 stop12h 37m

$169

MolineChicago

MLI - ORD

MLIORD

Moline Quad-City

Sat 7/26

11:26 am-12:35 pm

Nonstop1h 09m

Chicago O'Hare Intl

Sat 8/2

10:00 pm-10:58 pm

Nonstop0h 58m

$179

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Fri 3/28

5:45 am-7:07 am

Nonstop1h 22m

Chicago O'Hare Intl

Sun 3/30

12:57 pm-2:22 pm

Nonstop1h 25m

$189

MolineChicago

MLI - ORD

MLIORD

Moline Quad-City

Fri 3/7

3:50 pm-4:57 pm

Nonstop1h 07m

Chicago O'Hare Intl

Tue 3/11

9:05 am-10:19 am

Nonstop1h 14m

$190

Sioux CityChicago

SUX - ORD

SUXORD

Sioux City Sioux Gateway

Mon 4/14

10:03 am-11:42 am

Nonstop1h 39m

Chicago O'Hare Intl

Mon 4/28

8:40 pm-10:26 pm

Nonstop1h 46m

$194

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Fri 3/21

2:40 pm-4:05 pm

Nonstop1h 25m

Chicago Midway

Fri 3/28

4:05 pm-5:35 pm

Nonstop1h 30m

$207

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Fri 3/21

10:47 am-12:28 pm

Nonstop1h 41m

Chicago O'Hare Intl

Fri 3/28

6:35 pm-8:25 pm

Nonstop1h 50m

$207

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Tue 4/1

6:20 am-12:36 pm

1 stop6h 16m

Chicago Midway

Sat 4/5

1:12 pm-5:19 pm

1 stop4h 07m

$209

Des MoinesChicago

DSM - ORD

DSMORD

Des Moines

Sat 4/26

12:30 pm-4:11 pm

1 stop3h 41m

Chicago O'Hare Intl

Wed 4/30

6:35 am-11:19 am

1 stop4h 44m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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.

Travel insights for flights from Iowa to Chicago

Get recent, data-driven insights about flights from Iowa to Chicago including ideal travel times, pricing trends, and more.

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

Currently, August is the cheapest month in which you can book a flight from Iowa to Chicago (average of $245). Flying from Iowa to Chicago in March is currently the most expensive (average of $321). 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 20, 2025.

When flying from Iowa to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 20, 2025.

The most flights from USIA to CHI are scheduled on a Wednesday (36 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated February 20, 2025.
Read reviews from past customers who have flown Southwest, Alaska Airlines and Delta from Iowa to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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.

  • 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 Frontier ($55), Denver Air Connection ($64), and Southwest ($89).

  • 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 Omaha Eppley Airfield - Chicago Midway 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: Piedmont Airlines (100%), Qatar Airways (93%), Envoy Air( 92%).

  • What are the cheapest flights from Iowa to Chicago?

    Looking for the cheapest flight from Iowa to Chicago? While on average our users pay $1,273, our data indicates the cheapest price to be $134. The most popular route (Omaha Eppley Airfield - Chicago O'Hare Intl), is priced around $177.

  • 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, August is the cheapest month in which you can book a flight from Iowa to Chicago (average of $245). Flying from Iowa to Chicago in March is currently the most expensive (average of $321). 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 Iowa?

Book flights to Iowa if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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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Denver to Midway flights

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 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Southern / MokuleleCheapest$72Average$134FlexibilityNo cancel feeOn-timeN/A
Denver Air ConnectionCheapest$129Average$172FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$147Average$249FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$310FlexibilityNo cancel feeOn-time71%
DeltaCheapest$195Average$562FlexibilityNo cancel feeOn-timeN/A
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