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

Direct flights are often convenient, saving 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 flexible with your travel time.

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

Yes, being flexible with your travel dates can significantly impact flight prices. Flying on weekdays or during off-peak seasons often results in lower fares compared to weekends or holidays. Adjusting your departure or return by a day or two may reveal better deals.

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. Also, consider transportation costs to and from the airports. These additional expenses can sometimes add up and affect the total cost of your trip.

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 2 days ago

451 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 17, 2026.)

Today’s best flight deals from Des Moines to Chicago

Explore current cheapest deals departing from Des Moines to Chicago

2026-09-11 – 2026-09-14
DSM - Chicago
73% AI deal score
$368
$168
Round trip
2026-09-10 – 2026-09-12
DSM - Chicago
72% AI deal score
$369
$174
Round trip
2026-09-10 – 2026-09-14
DSM - Chicago
71% AI deal score
$369
$182
Round trip
2026-09-18 – 2026-09-21
DSM - Chicago
75% AI deal score
$367
$193
Round trip
2026-09-11 – 2026-09-14
DSM - Chicago
42% AI deal score
$203
$206
Round trip
2026-09-21 – 2026-09-23
DSM - Chicago
44% AI deal score
$209
$215
Round trip
2026-09-14 – 2026-09-16
DSM - Chicago
44% AI deal score
$211
$215
Round trip
2026-09-07 – 2026-09-09
DSM - Chicago
44% AI deal score
$214
$215
Round trip
2026-09-22 – 2026-09-24
DSM - Chicago
42% AI deal score
$201
$215
Round trip
2026-09-15 – 2026-09-17
DSM - Chicago
42% AI deal score
$203
$215
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: $298 - $577

Prices are currently below the regular range.

The regular price range for flights from Des Moines to Chicago is $298 to $577. The current lowest deal is $168 with Frontier Airlines for travel from Sep 11-Sep 14.

now $168

Low $298

High $577

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

Fri, Aug 21

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

Frontier Airlines

$663

$469

One-way

Sun, Aug 23

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

Allegiant Air

$520

$459

One-way

Mon, Aug 24

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

Allegiant Air

$558

$507

One-way

Sat, Aug 29

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

$432

$391

One-way

Wed, Sep 2

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (MDW)

Southwest Airlines

$215

$258

One-way

Thu, Sep 3

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (RFD)

Allegiant Air

$394

$355

One-way

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

3 nights

Sep 11 - Sep 14

$369 → $168

55%

2 nights

Aug 21 - Aug 23

$663 → $469

29%

4 nights

Sep 10 - Sep 14

$368 → $182

51%

2 nights

Sep 10 - Sep 12

$368 → $182

51%

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 offers the lowest median prices

Historically, April, December, and March offer the lowest median prices for this route.

⏱️ Flight duration

Direct flights average 1h 31m

Direct flights typically take 1h 31m, while connecting flights average 5h 41m.

✈️ Airlines & availability

Connecting flights are more common

About 30.7% of recent flights are direct, with connecting flights being more common.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines is a direct carrier option for flights from Des Moines to Chicago.

🎯 Booking tip

Deals appear frequently on this route

Deals for flights from Des Moines to Chicago appear frequently, typically every 30 days.

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

Aug 18

Chicago, United States

69% AI deal score

$1,855

$1,126

Save $729

From DSM

Elite

Nov 05

Chicago, United States

45% AI deal score

$506

$492

Save $14

United Airlines

Business Class

From DSM

Elite

Oct 01

Chicago, United States

44% AI deal score

$487

$481

Save $6

United Airlines

Business Class

From DSM

Elite

Sep 15

Chicago, United States

44% AI deal score

$484

$481

Save $3

United Airlines

Business Class

From DSM

Elite

Sep 16

Chicago, United States

43% AI deal score

$481

United Airlines

Business Class

From DSM

Elite

Nov 20

Chicago, United States

43% AI deal score

$520

United Airlines

Business Class

From DSM

Elite

Sep 21

Chicago, United States

43% AI deal score

$2,049

WestJet, +1

Business Class

From DSM

Elite

Oct 10

Chicago, United States

43% AI deal score

$2,089

WestJet, +1

Business Class

From DSM

Elite

Sep 21

Chicago, United States

43% AI deal score

$2,133

WestJet, +1

Business Class

From DSM

Elite

Sep 11

Chicago, United States

42% AI deal score

$545

United Airlines

Business Class

From DSM

Elite

Sep 04

Chicago, United States

42% AI deal score

$563

United Airlines

Business Class

From DSM

Elite

Sep 02

Chicago, United States

42% AI deal score

$564

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

To find more affordable flights, consider being flexible with your travel dates and times. Using flight comparison sites can help you compare prices across various airlines and booking platforms. Looking into different departure or arrival airports may also reveal lower fares.

Booking flights in advance often provides better prices, though last-minute deals can sometimes appear. Prices may fluctuate, so monitoring fares over a period can help you identify optimal booking times. Mid-week travel days sometimes offer more competitive rates.

Yes, comparing nearby airports can often lead to more flight options and potentially lower prices. Sometimes, flying into or out of a slightly more distant airport can result in significant savings. Always consider the additional travel time and cost to reach these 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: $298 - $577

Prices are currently below the regular range.

The regular price range for flights from Des Moines to Chicago is $298 to $577. The current lowest deal is $168 with Frontier Airlines for travel from Sep 11-Sep 14.

now $168

Low $298

High $577

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

Fri, Aug 21

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

Frontier Airlines

$663

$469

One-way

Sun, Aug 23

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

Allegiant Air

$520

$459

One-way

Mon, Aug 24

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

Allegiant Air

$558

$507

One-way

Sat, Aug 29

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

$432

$391

One-way

Wed, Sep 2

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (MDW)

Southwest Airlines

$215

$258

One-way

Thu, Sep 3

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (RFD)

Allegiant Air

$394

$355

One-way

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

3 nights

Sep 11 - Sep 14

$369 → $168

55%

2 nights

Aug 21 - Aug 23

$663 → $469

29%

4 nights

Sep 10 - Sep 14

$368 → $182

51%

2 nights

Sep 10 - Sep 12

$368 → $182

51%

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 offers the lowest median prices

Historically, April, December, and March offer the lowest median prices for this route.

⏱️ Flight duration

Direct flights average 1h 31m

Direct flights typically take 1h 31m, while connecting flights average 5h 41m.

✈️ Airlines & availability

Connecting flights are more common

About 30.7% of recent flights are direct, with connecting flights being more common.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines is a direct carrier option for flights from Des Moines to Chicago.

🎯 Booking tip

Deals appear frequently on this route

Deals for flights from Des Moines to Chicago appear frequently, typically every 30 days.

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

Aug 18

Chicago, United States

69% AI deal score

$1,855

$1,126

Save $729

From DSM

Elite

Nov 05

Chicago, United States

45% AI deal score

$506

$492

Save $14

United Airlines

Business Class

From DSM

Elite

Oct 01

Chicago, United States

44% AI deal score

$487

$481

Save $6

United Airlines

Business Class

From DSM

Elite

Sep 15

Chicago, United States

44% AI deal score

$484

$481

Save $3

United Airlines

Business Class

From DSM

Elite

Sep 16

Chicago, United States

43% AI deal score

$481

United Airlines

Business Class

From DSM

Elite

Nov 20

Chicago, United States

43% AI deal score

$520

United Airlines

Business Class

From DSM

Elite

Sep 21

Chicago, United States

43% AI deal score

$2,049

WestJet, +1

Business Class

From DSM

Elite

Oct 10

Chicago, United States

43% AI deal score

$2,089

WestJet, +1

Business Class

From DSM

Elite

Sep 21

Chicago, United States

43% AI deal score

$2,133

WestJet, +1

Business Class

From DSM

Elite

Sep 11

Chicago, United States

42% AI deal score

$545

United Airlines

Business Class

From DSM

Elite

Sep 04

Chicago, United States

42% AI deal score

$563

United Airlines

Business Class

From DSM

Elite

Sep 02

Chicago, United States

42% AI deal score

$564

United Airlines

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 offers the lowest median prices

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

Aug 18

Nov 05

Oct 01

Sep 15

Sep 16

Nov 20

Sep 21

Oct 10

Sep 21

Sep 11

Sep 04

Sep 02

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 offers the lowest median prices

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

Aug 18

Nov 05

Oct 01

Sep 15

Sep 16

Nov 20

Sep 21

Oct 10

Sep 21

Sep 11

Sep 04

Sep 02

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?