What airlines fly to Chicago?

United Airlines, American Airlines and Contour are the top three most popular airlines that fly to Chicago from Iowa according to our data. United Airlines is the first choice among our users, with 63% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Iowa to Chicago on average per week?

The number of flights available between Iowa and Chicago is 531 per week as of November 2026. The most frequent departure day is Mon, with 18% of weekly flights leaving on this day.

How long does it take to fly to Chicago?

Average flight duration from Iowa to Chicago depends on which airport you fly into and out of. Flying from Dubuque to Chicago O'Hare Intl Airport is 50m on average, while flying from Cedar Rapids to Chicago O'Hare Intl Airport is 1h 16m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

What is the cheapest airline that flies from Iowa to Chicago?

Contour, American Airlines, and Southwest are the most popular carriers operating from Iowa to Chicago

How many flights depart from Iowa to Chicago on average per day?

75 flights are operational daily from Iowa to Chicago as of November 2026. The most popular departure time for this route is 9:00AM, with 45% of flights per day taking off at noon.

When did momondo last update prices for flights from Iowa to Chicago?

Prices for flights from Iowa to Chicago are refreshed on a daily basis.

How many operators does momondo search for flights from Iowa to Chicago?

The number of operators available for flights from Iowa to Chicago is 4 as of November 2026.

How old do you have to be to fly from Iowa to Chicago?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Iowa to Chicago.

What documentation or ID do you need to fly to Chicago?

The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$53 Cheap Flights from Iowa to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Iowa to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

3:45 pm - 5:20 pmBRL Burlington-ORD Chicago O'Hare Intl

1h 35mnonstop

6:00 pm - 7:25 pmORD Chicago O'Hare Intl-BRL Burlington

1h 25mnonstop

$107Contour

Tue, Nov 24 - Tue, Dec 1

9:00 am - 10:35 amBRL Burlington-ORD Chicago O'Hare Intl

1h 35mnonstop

6:00 pm - 7:25 pmORD Chicago O'Hare Intl-BRL Burlington

1h 25mnonstop

$108Contour

Tue, Nov 17 - Sat, Nov 21

3:30 pm - 5:00 pmDSM Des Moines-MDW Chicago Midway

1h 30mnonstop

9:35 pm - 11:05 pmMDW Chicago Midway-DSM Des Moines

1h 30mnonstop

$195Southwest

Thu, Nov 19 - Mon, Nov 23

9:31 am - 11:20 amDSM Des Moines-ORD Chicago O'Hare Intl

1h 49mnonstop

7:12 am - 8:53 amORD Chicago O'Hare Intl-DSM Des Moines

1h 41mnonstop

$195American Airlines

Thu, Nov 26 - Thu, Dec 3

7:24 pm - 9:14 pmDSM Des Moines-ORD Chicago O'Hare Intl

1h 50mnonstop

11:51 am - 1:28 pmORD Chicago O'Hare Intl-DSM Des Moines

1h 37mnonstop

$195American Airlines

Thu, Nov 19 - Mon, Nov 23

6:05 am - 7:42 amDSM Des Moines-ORD Chicago O'Hare Intl

1h 37mnonstop

4:00 pm - 5:28 pmORD Chicago O'Hare Intl-DSM Des Moines

1h 28mnonstop

$195United Airlines

Thu, Nov 19 - Mon, Nov 23

11:29 am - 1:04 pmFOD Fort Dodge-ORD Chicago O'Hare Intl

1h 35mnonstop

4:20 pm - 5:57 pmORD Chicago O'Hare Intl-FOD Fort Dodge

1h 37mnonstop

$198United Airlines

Fri, Dec 4 - Thu, Dec 10

3:30 pm - 5:00 pmDSM Des Moines-MDW Chicago Midway

1h 30mnonstop

5:55 am - 1:10 pmMDW Chicago Midway-DSM Des Moines

7h 15m1 stop Denver Intl

$205Southwest

Thu, Nov 19 - Mon, Nov 23

6:41 am - 11:59 amDSM Des Moines-MDW Chicago Midway

5h 18m1 stop Minneapolis St Paul

5:30 pm - 9:31 pmMDW Chicago Midway-DSM Des Moines

4h 01m1 stop Minneapolis St Paul

$215Delta

Sat, Dec 5 - Sat, Dec 5

4:53 pm - 9:35 pmDSM Des Moines-ORD Chicago O'Hare Intl

4h 42m1 stop Minneapolis St Paul

6:20 am - 10:21 amORD Chicago O'Hare Intl-DSM Des Moines

4h 01m1 stop Minneapolis St Paul

$215Delta

Thu, Dec 3 - Mon, Dec 7

Cheap last minute flights

Enter your travel dates to find the best prices.

9:00 am - 10:35 amBRL Burlington-ORD Chicago O'Hare Intl

1h 35mnonstop

6:00 pm - 7:25 pmORD Chicago O'Hare Intl-BRL Burlington

1h 25mnonstop

$154Contour

Sun, Nov 8 - Sun, Nov 15

3:45 pm - 5:20 pmBRL Burlington-ORD Chicago O'Hare Intl

1h 35mnonstop

6:00 pm - 7:25 pmORD Chicago O'Hare Intl-BRL Burlington

1h 25mnonstop

$189Contour

Fri, Nov 6 - Mon, Nov 9

6:04 am - 7:39 amALO Waterloo-ORD Chicago O'Hare Intl

1h 35mnonstop

1:47 pm - 3:13 pmORD Chicago O'Hare Intl-ALO Waterloo

1h 26mnonstop

$324American Airlines

Sat, Nov 7 - Sun, Nov 8

6:04 am - 7:39 amALO Waterloo-ORD Chicago O'Hare Intl

1h 35mnonstop

1:47 pm - 3:13 pmORD Chicago O'Hare Intl-ALO Waterloo

1h 26mnonstop

$324American Airlines

Sat, Nov 7 - Mon, Nov 9

8:30 pm - 12:21 amDSM Des Moines-ORD Chicago O'Hare Intl

27h 51m1 stop Denver Intl

7:00 am - 7:50 pmORD Chicago O'Hare Intl-DSM Des Moines

12h 50m1 stop Denver Intl

$330Frontier

Mon, Nov 9 - Sun, Dec 6

8:30 pm - 12:21 amDSM Des Moines-ORD Chicago O'Hare Intl

27h 51m1 stop Denver Intl

7:00 am - 7:50 pmORD Chicago O'Hare Intl-DSM Des Moines

12h 50m1 stop Denver Intl

$355Frontier

Fri, Nov 6 - Sun, Dec 6

6:00 am - 7:59 amSUX Sioux City Sioux Gateway-ORD Chicago O'Hare Intl

1h 59mnonstop

4:20 pm - 6:10 pmORD Chicago O'Hare Intl-SUX Sioux City Sioux Gateway

1h 50mnonstop

$394United Airlines

Sat, Nov 7 - Sat, Nov 14

9:22 am - 10:59 amMCW Mason City-ORD Chicago O'Hare Intl

1h 37mnonstop

7:09 am - 8:39 amORD Chicago O'Hare Intl-MCW Mason City

1h 30mnonstop

$402United Airlines

Sat, Nov 7 - Mon, Nov 9

4:25 pm - 5:45 pmDSM Des Moines-MDW Chicago Midway

1h 20mnonstop

8:40 pm - 10:05 pmMDW Chicago Midway-DSM Des Moines

1h 25mnonstop

$447Southwest

Mon, Nov 9 - Mon, Dec 7

5:25 am - 6:55 amDSM Des Moines-MDW Chicago Midway

1h 30mnonstop

10:05 am - 11:25 amMDW Chicago Midway-DSM Des Moines

1h 20mnonstop

$447Southwest

Fri, Nov 6 - Mon, Dec 7

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Frontier flights from Iowa to Chicago

Our best Frontier deals on Iowa to Chicago flight tickets

Frontier

Dec 17

DSM8:26 pmDes Moines

28h 00m

1 stop

ORD12:26 amChicago O'Hare Intl

Dec 20

ORD7:45 amChicago O'Hare Intl

11h 46m

1 stop

DSM7:31 pmDes Moines

$244

Frontier

Nov 13

DSM8:30 pmDes Moines

27h 51m

1 stop

ORD12:21 amChicago O'Hare Intl

Dec 3

ORD7:00 amChicago O'Hare Intl

12h 40m

1 stop

DSM7:40 pmDes Moines

$313

Frontier

Nov 9

DSM8:30 pmDes Moines

27h 51m

1 stop

ORD12:21 amChicago O'Hare Intl

Dec 6

ORD7:00 amChicago O'Hare Intl

12h 50m

1 stop

DSM7:50 pmDes Moines

$330

American Airlines flights from Iowa to Chicago

Our best American Airlines deals on Iowa to Chicago flight tickets

American Airlines

Nov 14

ALO6:04 amWaterloo

1h 35m

ORD7:39 amChicago O'Hare Intl

Nov 18

ORD1:47 pmChicago O'Hare Intl

1h 26m

ALO3:13 pmWaterloo

$224

American Airlines

Dec 18

DSM7:58 pmDes Moines

1h 42m

ORD9:40 pmChicago O'Hare Intl

Dec 25

ORD1:15 pmChicago O'Hare Intl

1h 37m

DSM2:52 pmDes Moines

$238

American Airlines

Dec 9

DSM9:23 amDes Moines

1h 47m

ORD11:10 amChicago O'Hare Intl

Dec 18

ORD5:29 pmChicago O'Hare Intl

1h 40m

DSM7:09 pmDes Moines

$239

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

BurlingtonChicago

BRL Burlington - ORD Chicago O'Hare Intl

BRLORD

Burlington

Tue 11/24

3:45 pm-5:20 pm

Nonstop1h 35m

Chicago O'Hare Intl

Tue 12/1

6:00 pm-7:25 pm

Nonstop1h 25m

$107

BurlingtonChicago

BRL Burlington - ORD Chicago O'Hare Intl

BRLORD

Burlington

Tue 11/17

9:00 am-10:35 am

Nonstop1h 35m

Chicago O'Hare Intl

Sat 11/21

6:00 pm-7:25 pm

Nonstop1h 25m

$108

Des MoinesChicago

DSM Des Moines - MDW Chicago Midway

DSMMDW

Des Moines

Thu 11/19

3:30 pm-5:00 pm

Nonstop1h 30m

Chicago Midway

Mon 11/23

9:35 pm-11:05 pm

Nonstop1h 30m

$195

Des MoinesChicago

DSM Des Moines - ORD Chicago O'Hare Intl

DSMORD

Des Moines

Thu 11/26

9:31 am-11:20 am

Nonstop1h 49m

Chicago O'Hare Intl

Thu 12/3

7:12 am-8:53 am

Nonstop1h 41m

$195

Des MoinesChicago

DSM Des Moines - ORD Chicago O'Hare Intl

DSMORD

Des Moines

Thu 11/19

7:24 pm-9:14 pm

Nonstop1h 50m

Chicago O'Hare Intl

Mon 11/23

11:51 am-1:28 pm

Nonstop1h 37m

$195

Des MoinesChicago

DSM Des Moines - ORD Chicago O'Hare Intl

DSMORD

Des Moines

Thu 11/19

6:05 am-7:42 am

Nonstop1h 37m

Chicago O'Hare Intl

Mon 11/23

4:00 pm-5:28 pm

Nonstop1h 28m

$195

Fort DodgeChicago

FOD Fort Dodge - ORD Chicago O'Hare Intl

FODORD

Fort Dodge

Fri 12/4

11:29 am-1:04 pm

Nonstop1h 35m

Chicago O'Hare Intl

Thu 12/10

4:20 pm-5:57 pm

Nonstop1h 37m

$198

Des MoinesChicago

DSM Des Moines - MDW Chicago Midway

DSMMDW

Des Moines

Thu 11/19

3:30 pm-5:00 pm

Nonstop1h 30m

Chicago Midway

Mon 11/23

5:55 am-1:10 pm

1 stop7h 15m

$205

Des MoinesChicago

DSM Des Moines - MDW Chicago Midway

DSMMDW

Des Moines

Sat 12/5

6:41 am-11:59 am

1 stop5h 18m

Chicago Midway

Sat 12/5

5:30 pm-9:31 pm

1 stop4h 01m

$215

Des MoinesChicago

DSM Des Moines - ORD Chicago O'Hare Intl

DSMORD

Des Moines

Thu 12/3

4:53 pm-9:35 pm

1 stop4h 42m

Chicago O'Hare Intl

Mon 12/7

6:20 am-10:21 am

1 stop4h 01m

$215

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Iowa to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Iowa, with most prices found around $239. If you’re not able to fly to Chicago in February, then December is your next best option. Flight prices from Iowa to Chicago during December average around $264.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $513. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Iowa to Chicago for around $691.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Iowa to Chicago during this time can be as low as $512. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $1,099.

What is the cheapest Iowa to Chicago flight route?

Fly from Burlington to Chicago O'Hare Intl for the best Iowa - Chicago flight prices

How far in advance should I book a flight from Iowa to Chicago?

You are more likely to see cheaper flights to Chicago from Iowa when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $355 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Iowa for as low as $256 on momondo.

What cabin class options are available on Iowa to Chicago flights?

There are 4 cabin classes available to choose from on Iowa to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Iowa to Chicago flights?

No. A direct flight is the cheapest option for a flight between Iowa to Chicago.

Cheap Iowa to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Iowa to Chicago

Best Price Found	$53
Fastest flight time	0h 50m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Iowa in the past 72 hours is $53. The best round-trip flight deal from Iowa to Chicago found on momondo in the last 72 hours is $107.

The fastest flight from Iowa to Chicago takes 0h 50m

Direct flights go from Iowa to Chicago every day.

There are 3 airports in Chicago. From Iowa there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying from Iowa to Chicago

When did momondo last update prices for flights from Iowa to Chicago?
Prices for flights from Iowa to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Iowa to Chicago?
The number of operators available for flights from Iowa to Chicago is 4 as of November 2026.
How old do you have to be to fly from Iowa to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Iowa to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Iowa to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Iowa to Chicago is Embraer 175, representing 14.52% of all bookings. The subsequent popular models are Canadair (Bombardier) Regional Jet 700 at 13.21%, Airbus A319 at 12.20%, and Embraer 175 (Enhanced Winglets) at 10.84%.

Best airlines flying from Iowa to Chicago

Compare and see reviews for airlines that fly from Iowa to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Contour	PriceFrom $68	Free Cancellation	Rating 7.6 44 reviews	Search Contour flights
American Airlines	PriceFrom $148	Free Cancellation	Rating 7.0 12,228 reviews	Search American Airlines flights
United Airlines	PriceFrom $179	Free Cancellation	Rating 7.3 10,460 reviews	Search United Airlines flights
Southwest	PriceFrom $283	Free Cancellation	Rating 8.0 4,215 reviews	Search Southwest flights

Merrillville

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Hammond

Portage

Lansing

Saint Joseph

Benton Harbor

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Iowa to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Iowa.

Can I find flights from Iowa to Chicago with flexible booking policies on momondo?

Flights from Iowa to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Iowa to Chicago?

Once you have performed a search for Iowa to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Iowa to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Iowa. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from Iowa to Chicago from $53

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Iowa to Chicago departing on 11/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Frontier flights from Iowa to Chicago

Our best Frontier deals on Iowa to Chicago flight tickets

American Airlines flights from Iowa to Chicago

Our best American Airlines deals on Iowa to Chicago flight tickets

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See travel insights to Chicago from

How to get the cheapest flight ticket from Iowa to Chicago

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Iowa to Chicago flight route?

How far in advance should I book a flight from Iowa to Chicago?

What cabin class options are available on Iowa to Chicago flights?

Can stopping save me money on Iowa to Chicago flights?

What is the cheapest airline that flies from Iowa to Chicago?

What airlines fly to Chicago?

How many flights depart from Iowa to Chicago on average per day?

How many flights depart from Iowa to Chicago on average per week?

How long does it take to fly to Chicago?

Cheap Iowa to Chicago flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Iowa to Chicago

Best airlines flying from Iowa to Chicago

Compare and see reviews for airlines that fly from Iowa to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo

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