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Cheap Flights from Des Moines to Chicago

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Des Moines

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Prices updated 24 days ago

486,190 searches this week

171 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from Des Moines to Chicago

Explore current cheapest deals departing from Des Moines to Chicago

Round trip

Sort by: Cheapest

October 14 - October 20

Cheapest

DSM - Chicago

$413

$185

Round trip

September 15 - September 22

DSM - Chicago

$224

$210

Round trip

October 14 - October 29

Best

DSM - Chicago

$372

$221

Round trip

September 13 - October 13

DSM - Chicago

$318

$222

Round trip

August 26 - August 29

DSM - Chicago

$213

$233

Round trip

September 26 - September 29

DSM - Chicago

$241

$233

Round trip

September 13 - October 8

DSM - Chicago

$318

$241

Round trip

September 13 - October 4

DSM - Chicago

$318

$242

Round trip

July 15 - July 29

DSM - Chicago

$205

$253

Round trip

July 14 - July 21

Earliest

DSM - Chicago

$227

$253

Round trip

Unlock all 500+ flight deals to Chicago and get alerts when great deals appear

Route Intelligence — 486,190 Searches this Week

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. This means you can expect a relatively quick journey, connecting two major Midwestern cities.

For cheap flights from Des Moines to Chicago, fares typically range from $222 to $435, with a median price of $326. Right now, current fares are near the typical level for this route. Approximately 4% of recent fares were classified as a good price, indicating that competitive deals are available, and new deals appear almost daily.

When is the cheapest time to fly from Des Moines to Chicago? Historically, the most affordable month to fly is April, with a median fare of $246. Following closely, December offers a median fare of $279, and March presents a median of $295.

A meaningful share of itineraries are non-stop, with 50.7% of recent fares being direct flights from Des Moines to Chicago. For the remaining itineraries that include connections, the typical number of stopovers is 3.

How long is the flight from Des Moines to Chicago? A typical journey, including connections, takes approximately 3h 13m. This duration accounts for both direct services and itineraries with stopovers, providing a realistic expectation for your travel time.

How much is a round trip from Des Moines to Chicago

Regular price: $335 - $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 between $335 and $572. The current lowest deal is $185 with Frontier Airlines, for travel from Oct 14-Oct 20.

now $185

Low $335

High $572

The cheapest time to fly from Des Moines to Chicago

The cheapest month to fly from Des Moines to Chicago is April, with a median price of $246. The most expensive month is June, with a median price of $477. Prices are generally lower from March to December.

April

Cheapest

Flights from $246

June

Most Expensive

Flights from $477

Jan

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Des Moines to Chicago

American Airlines

Last-minute flights going from Des Moines to Chicago

Wed, Jun 17

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (RFD)

Allegiant Air

$455

$319

One-way

Fri, Jun 19

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

Allegiant Air

$487

$406

One-way

Wed, Jul 1

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (RFD)

Allegiant Air

$398

$328

One-way

Fri, Jul 3

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

Frontier Airlines

$380

$312

One-way

Fri, Jul 3

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (MDW)

$405

$355

One-way

Thu, Jul 9

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

Deutsche Luft Hansa

$352

$351

One-way

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

6 nights

Oct 14 - Oct 20

$413 → $185

55%

2 nights

Oct 9 - Oct 11

$426 → $271

36%

15 nights

Oct 14 - Oct 29

$372 → $221

41%

7 nights

Jun 17 - Jun 24

$455 → $319

30%

Popular Airports to fly from Des Moines to Chicago

Des Moines - Chicago route insights

💸 Price insights

Recent fares are near the typical level

Recent fares from Des Moines to Chicago are near the typical level, with a median price of $326.

📅 Best time to fly

April is historically the cheapest month to fly

Historically, April is the cheapest month to fly from Des Moines to Chicago, with a median price of $246.

⏱️ Flight duration

Typical flight time is 3h 13m

The typical flight duration from Des Moines to Chicago is 3 hours and 13 minutes.

✈️ Airlines & availability

50.7% of deals are direct flights

Approximately 50.7% of deals for this route are direct flights, with connecting flights having a median of 3 stopovers.

🏆 Airline highlight

American Airlines offers direct flights

American Airlines offers direct flights from Des Moines to Chicago.

🎯 Booking tip

Deals appear frequently for this route

Deals for flights from Des Moines to Chicago appear frequently, with about 0.9 deals per day.

Des Moines main airports to depart from

Des Moines International (DSM)

Cheapest

Des Moines International is a convenient option for flights from Des Moines to Chicago.

📍 ~8 km from city center (reachable by car)

💸 Flights from ~$185

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

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

📍 ~27 km from Chicago (reachable by car, train, bus)

💸 Flights from ~$185

Chicago Midway International (MDW)

Chicago Midway International Airport offers another convenient option for reaching Chicago from Des Moines.

📍 ~14 km from Chicago (reachable by car, train, bus)

💸 Flights from ~$233

Chicago Rockford International (RFD)

Chicago Rockford International Airport provides an alternative arrival point for flights to the Chicago area.

📍 ~120 km from Chicago (reachable by car, bus)

💸 Flights from ~$242

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers excellent proximity to Chicago with high-frequency flight options and direct rail access.

📍 ~135 km from Chicago (reachable by rail)

💸 Flights from ~$271

South Bend International (SBN)

South Bend International is the geographically closest alternative, directly connected to downtown Chicago via commuter rail.

📍 ~120 km from Chicago (reachable by rail)

💸 Flights from ~$280

Gerald R. Ford International (GRR)

Cheapest

Gerald R. Ford International is a major regional hub, a good alternative for travelers on Chicago's eastern side.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$195

Dane County Regional (MSN)

Dane County Regional is a reliable regional airport with consistent service, less congested than Chicago or Milwaukee.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$281

Fort Wayne International (FWA)

Fort Wayne International offers stable regional service, an alternative for travelers in the southeastern Chicago suburbs.

📍 ~220 km from Chicago (reachable by car)

💸 Flights from ~$289

Business & First Class Flight Deals to Chicago

44% AI deal score

$505

From DSM

Chicago, United States

42% AI deal score

$1,060

$971

Save $89

From DSM

Elite

Jul 16

Chicago, United States

41% AI deal score

$550

From DSM

Elite

Jun 30

Chicago, United States

41% AI deal score

$637

From DSM

Elite

Jul 14

Chicago, United States

40% AI deal score

$623

From DSM

Chicago, United States

28% AI deal score

$2,416

From DSM

Elite

Jul 31

Chicago, United States

28% AI deal score

$2,843

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Des Moines to Chicago is typically 14-27 days before departure. During this period, the average price for tickets was around $235. Booking 7-13 days out saw an average price of $280, while waiting until 0-6 days before departure increased the average price to $335. Conversely, booking more than 60 days in advance resulted in higher average prices, around $425.

Across the trailing quarter, a flight from Des Moines to Chicago is considered a good deal if it is priced at or below $222. The median price for this route over the trailing 90 days was $326. Prices above $435 typically fall into the more expensive range for this route. Travelers can use the $222 threshold as a benchmark for identifying favorable prices.

Historically, April has been the cheapest month to fly from Des Moines to Chicago, with a median price of $246. December also offered relatively lower prices, with a median of $279. The annual median price for this route across the trailing 270 days was $326, indicating that April and December typically present more economical options for travelers.

Related routes

Consider alternative routes from Des Moines

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Cheap Flights from Des Moines to Chicago

Today’s best flight deals from Des Moines to Chicago

Unlock all 500+ flight deals to Chicago and get alerts when great deals appear

Route Intelligence — 486,190 Searches this Week

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 near the typical level

April is historically the cheapest month to fly

Typical flight time is 3h 13m

50.7% of deals are direct flights

American Airlines offers direct flights

Deals appear frequently for 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

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Frequently Asked Questions About Flights to Chicago

When should I buy Des Moines to Chicago tickets?

When should I buy Des Moines to Chicago tickets?

How do I know if a Des Moines to Chicago flight is a good deal?

How do I know if a Des Moines to Chicago flight is a good deal?

What's the cheapest month to fly from Des Moines to Chicago?