HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$64+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Iowa to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 July 3, 2025.

Round-trip from

$168
(Southwest)

One-way from

$64
(Mytrip)

Popular in

August

Cheapest in

May

Average price

$289

Good round-trip deal

$318 or less

Good one-way deal

$153 or less
From Iowa to Chicago (CHI)
Search Deals
One-way flight from Iowa to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($15 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 July 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

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 July 3, 2025.

This Southwest deal was found by Cheapflights users on 7/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/97:25 amOMA - MDW
Nonstop1h 25mSouthwest
Mon 8/119:00 pmMDW - OMA
Nonstop1h 25mSouthwest
Deal found 7/2$168
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Sat 8/233:18 pmOMA - ORD
Nonstop1h 47mUnited Airlines
Mon 8/258:05 pmORD - OMA
Nonstop1h 43mUnited Airlines
Deal found 6/30$168
This Southwest deal was found by Cheapflights users on 6/30. 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 8/215:20 amOMA - ORD
2 stops11h 05mSouthwest
Mon 8/252:55 pmORD - OMA
2 stops8h 00mSouthwest
Deal found 6/30$173
This Delta deal was found by Cheapflights users on 7/1. 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.
Thu 8/76:30 amOMA - MDW
1 stop5h 59mDelta
Tue 8/129:31 amMDW - OMA
1 stop3h 57mDelta
Deal found 7/1$177
This Delta deal was found by Cheapflights users on 7/1. 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.
Wed 9/36:30 amOMA - ORD
1 stop3h 50mDelta
Tue 9/96:10 amORD - OMA
1 stop4h 03mDelta
Deal found 7/1$177
This American Airlines deal was found by Cheapflights users on 7/3. 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.
Sun 8/1711:03 amCID - ORD
Nonstop1h 23mAmerican Airlines
Sun 8/249:15 amORD - CID
Nonstop1h 18mAmerican Airlines
Deal found 7/3$178
This American Airlines deal was found by Cheapflights users on 7/3. 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 10/311:20 amMLI - ORD
Nonstop1h 09mAmerican Airlines
Sat 10/119:55 amORD - MLI
Nonstop1h 04mAmerican Airlines
Deal found 7/3$179
This United Airlines deal was found by Cheapflights users on 7/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/256:37 amCID - ORD
Nonstop1h 25mUnited Airlines
Fri 8/298:05 pmORD - CID
Nonstop1h 20mUnited Airlines
Deal found 7/3$183
This American Airlines deal was found by Cheapflights users on 7/1. 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 7/299:03 amOMA - ORD
Nonstop1h 38mAmerican Airlines
Tue 8/510:28 pmORD - OMA
Nonstop1h 31mAmerican Airlines
Deal found 7/1$187
This Southwest deal was found by Cheapflights users on 7/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/163:45 pmDSM - MDW
1 stop5h 15mSouthwest
Wed 8/205:40 pmMDW - DSM
1 stop4h 40mSouthwest
Deal found 7/2$189
This Southwest deal was found by Cheapflights users on 7/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/166:10 amDSM - ORD
1 stop6h 55mSouthwest
Wed 8/207:00 amORD - DSM
1 stop7h 40mSouthwest
Deal found 7/2$189
This American Airlines deal was found by Cheapflights users on 7/1. 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 8/65:00 amDSM - ORD
Nonstop1h 30mAmerican Airlines
Sat 8/97:00 amORD - DSM
Nonstop1h 31mAmerican Airlines
Deal found 7/1$190

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 July 3, 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 - MDW

OMAMDW

Omaha Eppley Airfield

Sat 8/9

7:25 am-8:50 am

Nonstop1h 25m

Chicago Midway

Mon 8/11

9:00 pm-10:25 pm

Nonstop1h 25m

$168

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Sat 8/23

3:18 pm-5:05 pm

Nonstop1h 47m

Chicago O'Hare Intl

Mon 8/25

8:05 pm-9:48 pm

Nonstop1h 43m

$168

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Thu 8/21

5:20 am-4:25 pm

2 stops11h 05m

Chicago O'Hare Intl

Mon 8/25

7:00 am-7:05 pm

1 stop12h 05m

$173

OmahaChicago

OMA - MDW

OMAMDW

Omaha Eppley Airfield

Thu 8/7

6:30 am-12:29 pm

1 stop5h 59m

Chicago Midway

Tue 8/12

9:31 am-1:28 pm

1 stop3h 57m

$177

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Wed 9/3

6:30 am-10:20 am

1 stop3h 50m

Chicago O'Hare Intl

Tue 9/9

6:10 am-10:13 am

1 stop4h 03m

$177

Cedar RapidsChicago

CID - ORD

CIDORD

Cedar Rapids

Sun 8/17

11:03 am-12:26 pm

Nonstop1h 23m

Chicago O'Hare Intl

Sun 8/24

9:15 am-10:33 am

Nonstop1h 18m

$178

MolineChicago

MLI - ORD

MLIORD

Moline Quad-City

Wed 8/6

11:21 am-12:31 pm

Nonstop1h 10m

Chicago O'Hare Intl

Sun 8/10

10:35 pm-11:38 pm

Nonstop1h 03m

$179

Cedar RapidsChicago

CID - ORD

CIDORD

Cedar Rapids

Fri 7/25

6:37 am-8:02 am

Nonstop1h 25m

Chicago O'Hare Intl

Fri 8/29

8:05 pm-9:25 pm

Nonstop1h 20m

$183

OmahaChicago

OMA - ORD

OMAORD

Omaha Eppley Airfield

Tue 7/29

9:03 am-10:41 am

Nonstop1h 38m

Chicago O'Hare Intl

Tue 8/5

10:28 pm-11:59 pm

Nonstop1h 31m

$187

Des MoinesChicago

DSM - MDW

DSMMDW

Des Moines

Sat 8/16

3:45 pm-9:00 pm

1 stop5h 15m

Chicago Midway

Wed 8/20

5:40 pm-10:20 pm

1 stop4h 40m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 58 results
1
2
3
...
6

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, 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 July 3, 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 July 3, 2025.

The most flights from USIA to CHI are scheduled on a Thursday (46 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (7 on average).

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

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 July 3, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Iowa to Chicago by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.3
Good
708 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 ($64), Southwest ($69), and United Airlines ($69).

  • 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 Des Moines - 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: Copa Airlines (97%), Avianca (95%), GoJet( 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 $1,252, our data indicates the cheapest price to be $157. The most popular route (Omaha Eppley Airfield - Chicago O'Hare Intl), is priced around $137.

  • 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
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Iowa to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Philadelphia to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Boston to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Seattle to O'Hare Intl flights
Newark to Midway flights
Hobby to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Denver to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Atlanta to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Ontario to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Austin to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Tampa to O'Hare Intl flights
Dulles Intl to Midway flights
Burbank to O'Hare Intl flights
Los Angeles to Midway flights
Atlanta to O'Hare Intl flights
Miami to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
LaGuardia to Midway flights
Charlotte to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Hobby to Midway flights
Minneapolis to O'Hare Intl flights
Denver to Midway flights
San Diego to O'Hare Intl flights
Philadelphia to Midway flights
Orlando to O'Hare Intl flights
Baltimore to Midway flights
Portland to O'Hare Intl flights
San Francisco to Midway flights
San Jose to O'Hare Intl flights
Tampa to Midway flights
Oakland to O'Hare Intl flights
Newark to St. Louis flights
Hartford to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Love Field to O'Hare Intl flights
LaGuardia to St. Louis flights

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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Southern / MokuleleCheapest$72Average$103FlexibilityNo cancel feeOn-timeN/A
Denver Air ConnectionCheapest$129Average$170FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$147Average$257FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$290FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.