Are direct flights from Des Moines to Chicago always the best option?

Direct flights offer convenience by minimizing travel time and avoiding layovers. However, they are not always the cheapest option. Flights with one or more stops can sometimes be more affordable, especially if you are willing to spend extra time in transit. Consider your priorities for cost versus convenience.

Can flexible travel dates help on Des Moines to Chicago flights?

Yes, having flexible travel dates can often significantly impact the price of your flight. Mid-week flights or those during off-peak seasons usually offer lower fares compared to weekends or popular holiday periods. Adjusting your departure or return by a day or two may reveal cheaper options.

What extra costs should I check before booking Des Moines to Chicago flights?

Before booking, always check for potential extra costs such as baggage fees, seat selection charges, and in-flight services. Some airlines may also charge for printing boarding passes at the airport. Understanding these additional expenses can help you calculate the total cost of your trip accurately.

Flights From Des Moines

To Chicago

Cheap Flights from Des Moines to Chicago

Browse current best options from Des Moines. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Des Moines

RatePunk searches hundreds of travel sites at once for deals on flights to Chicago

Prices updated today

456 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Aug 31, 2026.)

Today’s best flight deals from Des Moines to Chicago

Explore current cheapest deals departing from Des Moines to Chicago

2026-09-28 – 2026-09-30
DSM - Chicago
75% AI deal score
$368
$198
Round trip
2026-10-09 – 2026-10-16
DSM - Chicago
72% AI deal score
$359
$229
Round trip
2026-10-23 – 2026-10-30
DSM - Chicago
71% AI deal score
$359
$231
Round trip
2026-11-06 – 2026-11-09
DSM - Chicago
71% AI deal score
$347
$232
Round trip
2026-10-08 – 2026-10-15
DSM - Chicago
41% AI deal score
$203
$234
Round trip
2026-10-12 – 2026-10-13
DSM - Chicago
42% AI deal score
$215
$234
Round trip
2026-10-13 – 2026-10-14
DSM - Chicago
43% AI deal score
$219
$234
Round trip
2026-10-22 – 2026-10-26
DSM - Chicago
43% AI deal score
$218
$234
Round trip
2026-10-19 – 2026-10-21
DSM - Chicago
43% AI deal score
$220
$234
Round trip
2026-10-07 – 2026-10-14
DSM - Chicago
42% AI deal score
$204
$234
Round trip

Des Moines to Chicago: Overview

Insights for flights from Des Moines to Chicago

Flights from Des Moines to Chicago cover a distance of 491 kilometers, classifying this as a short-haul route. Right now, fares for cheap flights from Des Moines to Chicago typically range from $323 to $517, with a median price of $408. Current fares are below the typical level, and only 2% of recent fares were classified as a good price.

When is the cheapest time to fly from Des Moines to Chicago? Historically, the most affordable months to fly this route are April, with a median fare of $246, followed by December at $279, and March at $295.

Most itineraries on this route connect at least once, with only 30.7% of recent fares being direct flights from Des Moines to Chicago. For connecting itineraries, the typical number of connections is 3.

A typical journey from Des Moines to Chicago, including connections, takes approximately 5h 41m. For those flying non-stop, the flight time is considerably shorter, at 1h 31m.

How much is a round trip from Des Moines to Chicago

Regular price: $295 - $572

Prices for flights from Des Moines to Chicago are currently below the regular range.

The regular price range for flights from Des Moines to Chicago is typically between $295 and $572. Currently, the lowest deal is $198 with Frontier Airlines for travel from Sep 28-Sep 30.

now $198

Low $295

High $572

The cheapest time to fly from Des Moines to Chicago

The cheapest month to fly from Des Moines to Chicago is January, with a median price of $295. The most expensive month is June, with a median price of $480. Prices are generally lower from January to December.

January

Cheapest

Flights from $295

June

Most Expensive

Flights from $480

Jan

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Des Moines to Chicago

United Airlines

Last-minute flights going from Des Moines to Chicago

Tue, Sep 1

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

$629

$567

One-way

Thu, Sep 3

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

$604

$530

One-way

Fri, Sep 4

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

Frontier Airlines

$604

$476

One-way

Sat, Sep 5

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

$545

$513

One-way

Sun, Sep 6

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (RFD)

Allegiant Air

$375

$286

One-way

Sun, Sep 6

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (RFD)

Allegiant Air

$520

$286

One-way

Biggest price drops on these dates for flights from Des Moines to Chicago

1 night

Aug 28 - Aug 29

$668 → $454

32%

1 night

Aug 26 - Aug 27

$715 → $547

24%

2 nights

Aug 28 - Aug 30

$663 → $527

21%

2 nights

Oct 1 - Oct 3

$380 → $247

35%

Popular Airports to fly from Des Moines to Chicago

Des Moines - Chicago route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from Des Moines to Chicago are below the typical level for this route.

📅 Best time to fly

April, December, and March are historically cheapest.

Historically, the cheapest months to fly are April ($246), December ($279), and March ($295).

⏱️ Flight duration

Direct flights average 1h 31m.

Direct flights to Chicago typically take 1 hour 31 minutes, connecting flights average 5 hours 41 minutes.

✈️ Airlines & availability

Connecting flights are more common.

Only 30.7% of recent flights from Des Moines to Chicago are direct, making connecting flights more common.

🏆 Airline highlight

United Airlines offers direct flights.

United Airlines is one carrier providing direct flights on the Des Moines to Chicago route.

🎯 Booking tip

Deals appear frequently on this route.

Deals for flights from Des Moines to Chicago are frequent, appearing often over a 30-day window.

Des Moines main airports to depart from

Des Moines International (DSM)

Cheapest

Des Moines International Airport is a convenient departure point for flights to Chicago.

📍 ~8 km from Des Moines (reachable by car)

💸 Flights from ~$202

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights to Chicago from Des Moines.

📍 ~25 km from Chicago city center (reachable by car or public transport).

💸 Flights from ~$182

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Cheapest

General Mitchell International Airport is a major international airport with significant carrier presence and direct flight options.

📍 ~135 km from Chicago (reachable by car or train)

💸 Flights from ~$245

Business & First Class Flight Deals to Chicago

Discover luxury on the budget with premium cabin class on flights from Des Moines to Chicago.

Elite

Best Elite deals to Chicago

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From DSM

Elite

Sep 21

Chicago, United States

43% AI deal score

$525

United Airlines

Business Class

From DSM

Elite

Nov 04

Chicago, United States

43% AI deal score

$531

United Airlines

Business Class

From DSM

Elite

Oct 06

Chicago, United States

43% AI deal score

$1,845

WestJet, +1

Business Class

From DSM

Elite

Oct 13

Chicago, United States

42% AI deal score

$525

United Airlines

Business Class

From DSM

Elite

Oct 08

Chicago, United States

42% AI deal score

$531

United Airlines

Business Class

From DSM

Elite

Sep 29

Chicago, United States

42% AI deal score

$531

United Airlines

Business Class

From DSM

Elite

Dec 08

Chicago, United States

42% AI deal score

$531

United Airlines

Business Class

From DSM

Elite

Oct 29

Chicago, United States

42% AI deal score

$531

United Airlines

Business Class

From DSM

Elite

Oct 14

Chicago, United States

42% AI deal score

$531

United Airlines

Business Class

From DSM

Elite

Sep 19

Chicago, United States

42% AI deal score

$2,112

WestJet, +1

Business Class

From DSM

Elite

Sep 19

Chicago, United States

42% AI deal score

$2,134

WestJet, +1

Business Class

From DSM

Elite

Oct 18

Chicago, United States

42% AI deal score

$2,141

WestJet, +1

Business Class

Frequently Asked Questions About Flights to Chicago

To find more affordable flights, consider being flexible with your travel dates and times. Comparing prices across different airlines and booking sites can also help you identify better deals. Sometimes, flying on weekdays or during off-peak hours may result in lower fares.

Booking flights in advance, often several weeks or months before your intended departure, can sometimes lead to better prices. However, prices can fluctuate, so monitoring fares over time may help you decide the optimal booking moment. Last-minute deals are less common but can occasionally appear.

Comparing nearby airports at both your origin and destination can sometimes uncover more economical flight options. While it may add to your ground travel time, the potential savings on airfare can be significant. Always factor in the cost and convenience of transportation to and from alternative airports.

Related routes

More routes from Des Moines

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Flights to Chicago from other cities

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Des Moines to Chicago: Overview

Insights for flights from Des Moines to Chicago

A typical journey from Des Moines to Chicago, including connections, takes approximately 5h 41m. For those flying non-stop, the flight time is considerably shorter, at 1h 31m.

How much is a round trip from Des Moines to Chicago

Regular price: $295 - $572

Prices for flights from Des Moines to Chicago are currently below the regular range.

The regular price range for flights from Des Moines to Chicago is typically between $295 and $572. Currently, the lowest deal is $198 with Frontier Airlines for travel from Sep 28-Sep 30.

now $198

Low $295

High $572

The cheapest time to fly from Des Moines to Chicago

January

Cheapest

Flights from $295

June

Most Expensive

Flights from $480

Jan

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Des Moines to Chicago

United Airlines

Last-minute flights going from Des Moines to Chicago

Tue, Sep 1

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

$629

$567

One-way

Thu, Sep 3

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

$604

$530

One-way

Fri, Sep 4

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

Frontier Airlines

$604

$476

One-way

Sat, Sep 5

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

$545

$513

One-way

Sun, Sep 6

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (RFD)

Allegiant Air

$375

$286

One-way

Sun, Sep 6

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (RFD)

Allegiant Air

$520

$286

One-way

Biggest price drops on these dates for flights from Des Moines to Chicago

1 night

Aug 28 - Aug 29

$668 → $454

32%

1 night

Aug 26 - Aug 27

$715 → $547

24%

2 nights

Aug 28 - Aug 30

$663 → $527

21%

2 nights

Oct 1 - Oct 3

$380 → $247

35%

Popular Airports to fly from Des Moines to Chicago

Des Moines - Chicago route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from Des Moines to Chicago are below the typical level for this route.

📅 Best time to fly

April, December, and March are historically cheapest.

Historically, the cheapest months to fly are April ($246), December ($279), and March ($295).

⏱️ Flight duration

Direct flights average 1h 31m.

Direct flights to Chicago typically take 1 hour 31 minutes, connecting flights average 5 hours 41 minutes.

✈️ Airlines & availability

Connecting flights are more common.

Only 30.7% of recent flights from Des Moines to Chicago are direct, making connecting flights more common.

🏆 Airline highlight

United Airlines offers direct flights.

United Airlines is one carrier providing direct flights on the Des Moines to Chicago route.

🎯 Booking tip

Deals appear frequently on this route.

Deals for flights from Des Moines to Chicago are frequent, appearing often over a 30-day window.

Des Moines main airports to depart from

Des Moines International (DSM)

Cheapest

Des Moines International Airport is a convenient departure point for flights to Chicago.

📍 ~8 km from Des Moines (reachable by car)

💸 Flights from ~$202

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights to Chicago from Des Moines.

📍 ~25 km from Chicago city center (reachable by car or public transport).

💸 Flights from ~$182

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Cheapest

General Mitchell International Airport is a major international airport with significant carrier presence and direct flight options.

📍 ~135 km from Chicago (reachable by car or train)

💸 Flights from ~$245

Chicago, United States

42% AI deal score

$2,141

WestJet, +1

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Des Moines to Chicago

Today’s best flight deals from Des Moines to Chicago

Des Moines to Chicago: Overview

Insights for flights from Des Moines to Chicago

How much is a round trip from Des Moines to Chicago

The cheapest time to fly from Des Moines to Chicago

Direct flights from Des Moines to Chicago

Last-minute flights going from Des Moines to Chicago

Biggest price drops on these dates for flights from Des Moines to Chicago

Popular Airports to fly from Des Moines to Chicago

Des Moines - Chicago route insights

Recent fares are below the typical level.

April, December, and March are historically cheapest.

Direct flights average 1h 31m.

Connecting flights are more common.

United Airlines offers direct flights.

Deals appear frequently on this route.

Des Moines main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Sep 21

Nov 04

Oct 06

Oct 13

Oct 08

Sep 29

Dec 08

Oct 29

Oct 14

Sep 19

Sep 19

Oct 18

Frequently Asked Questions About Flights to Chicago

How can I find cheap flights from Des Moines to Chicago?

When should I book flights from Des Moines to Chicago?

Should I compare nearby airports for flights from Des Moines to Chicago?

Are direct flights from Des Moines to Chicago always the best option?

Can flexible travel dates help on Des Moines to Chicago flights?

What extra costs should I check before booking Des Moines to Chicago flights?

Related routes

More routes from Des Moines

Flights to Chicago from other cities

Des Moines to Chicago: Overview

Insights for flights from Des Moines to Chicago

How much is a round trip from Des Moines to Chicago

The cheapest time to fly from Des Moines to Chicago

Direct flights from Des Moines to Chicago

Last-minute flights going from Des Moines to Chicago

Biggest price drops on these dates for flights from Des Moines to Chicago

Popular Airports to fly from Des Moines to Chicago

Des Moines - Chicago route insights

Recent fares are below the typical level.

April, December, and March are historically cheapest.

Direct flights average 1h 31m.

Connecting flights are more common.

United Airlines offers direct flights.

Deals appear frequently on this route.

Des Moines main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Sep 21

Nov 04

Oct 06

Oct 13

Oct 08

Sep 29

Dec 08

Oct 29

Oct 14

Sep 19

Sep 19

Oct 18

Frequently Asked Questions About Flights to Chicago

How can I find cheap flights from Des Moines to Chicago?

When should I book flights from Des Moines to Chicago?

Should I compare nearby airports for flights from Des Moines to Chicago?