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

Direct flights offer convenience by reducing travel time and avoiding layovers. However, they are not always the cheapest option, as flights with connections can sometimes be more affordable. Consider your priorities for cost versus convenience when choosing.

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

Yes, being flexible with your travel dates can significantly impact flight prices. Shifting your departure or return by a day or two may reveal cheaper fares. Weekday travel or flying during off-peak seasons usually offers more budget-friendly 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. Being aware of these additional fees can help you budget 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 5 days ago

402 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Jul 12, 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

August 24 - September 10

Cheapest

DSM - Chicago

$283

$191

Round trip

August 24 - September 17

Cheapest

DSM - Chicago

$276

$191

Round trip

August 24 - August 27

Best

DSM - Chicago

$353

$202

Round trip

September 13 - October 1

Best

DSM - Chicago

$312

$205

Round trip

September 3 - September 4

DSM - Chicago

$208

$206

Round trip

August 31 - September 29

DSM - Chicago

$276

$207

Round trip

August 26 - August 29

DSM - Chicago

$213

$208

Round trip

October 8 - October 14

DSM - Chicago

$229

$208

Round trip

August 4 - August 6

Earliest

DSM - Chicago

$226

$209

Round trip

August 22 - August 29

DSM - Chicago

$202

$209

Round trip

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

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–$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 cheapest month to fly is April, with a median fare of $246. December also offers lower prices, with a median of $279. Travelers can also find more affordable options in March, where the median fare is $295.

Most itineraries for this route connect at least once, with only 30.7% of recent fares being non-stop. For connecting itineraries, the typical number of connections is 3.

How long is the flight from Des Moines to Chicago? A typical journey from Des Moines to Chicago takes 1h 31m, including connections. For direct flights from Des Moines to Chicago, the median flight time is 1h 31m. Connecting itineraries, which are more common on this route, have a median journey time of 5h 41m.

How much is a round trip from Des Moines to Chicago

Regular price: $166 - $487

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

The regular price range for flights from Des Moines to Chicago is between $166 and $487. The current lowest deal is $209 on Kayak for travel from Aug 6-Aug 10.

now $209

Low $166

High $487

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. Generally, prices are 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

Last-minute flights going from Des Moines to Chicago

Mon, Aug 3

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

Allegiant Air

$345

$267

One-way

Tue, Aug 4

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

American Airlines

$224

$209

One-way

Wed, Aug 5

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (MDW)

$380

$227

One-way

Wed, Aug 5

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (MDW)

$341

$229

One-way

Wed, Aug 5

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (MDW)

$333

$229

One-way

Wed, Aug 5

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (MDW)

$381

$259

One-way

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

6 nights

Oct 14 - Oct 20

$391 → $210

46%

4 nights

Oct 16 - Oct 20

$410 → $230

44%

3 nights

Oct 5 - Oct 8

$393 → $244

38%

1 night

Jul 20 - Jul 21

$393 → $254

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 at $209.

📅 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

Nonstop flights average 1h 31m

Nonstop flights from Des Moines to Chicago typically take 1 hour and 31 minutes.

✈️ Airlines & availability

Connecting flights are more common

Connecting flights are more common for this route, with a median of 3 stopovers.

🏆 Airline highlight

No direct airline data available

Direct airline data is unavailable; consider deals from various providers for this route.

🎯 Booking tip

Deals appear frequently on this route

This route frequently has deals, with offers appearing often within 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

Chicago Midway International (MDW)

Cheapest

Chicago Midway International is a convenient arrival airport for flights to Chicago from Des Moines.

📍 ~14 km from Chicago city center (reachable by car)

💸 Flights from ~$209

Chicago Rockford International (RFD)

Chicago Rockford International offers another option for travelers flying from Des Moines to Chicago.

📍 ~126 km from Chicago city center (reachable by car)

O Hare International (ORD)

O Hare International is a major airport serving flights from Des Moines to Chicago.

📍 ~25 km from Chicago city center (reachable by car)

💸 Flights from ~$209

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Cheapest

General Mitchell International offers significant carrier presence and is easily accessible from Chicago.

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

💸 Flights from ~$204

Gerald R. Ford International (GRR)

Gerald R. Ford International provides a robust domestic network and strong presence of airlines.

📍 ~250 km from Chicago (reachable by car)

💸 Flights from ~$207

Dane County Regional (MSN)

Dane County Regional is a reliable regional hub with efficient operations and good amenities.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$309

South Bend International (SBN)

South Bend International is the closest alternative airport to the Chicago metro area.

📍 ~120 km from Chicago (reachable by car or train)

💸 Flights from ~$278

Fort Wayne International (FWA)

Fort Wayne International offers multiple cabin classes and solid connectivity for eastern domestic destinations.

📍 ~240 km from Chicago (reachable by car)

💸 Flights from ~$286

Business & First Class Flight Deals to Chicago

44% AI deal score

$1,951

From DSM

Elite

Jul 23

Chicago, United States

42% AI deal score

$1,138

$1,039

Save $99

From DSM

Elite

Jul 16

Chicago, United States

42% AI deal score

Chicago, United States

36% AI deal score

$5,306

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 offer lower fares.

Booking flights in advance often provides more competitive prices, especially for popular routes. However, prices can fluctuate, so monitoring fares over time may help you find a suitable deal. Last-minute bookings can sometimes be more expensive.

Comparing nearby airports can sometimes reveal additional flight options or potentially lower prices. While it may add to travel time, the savings could be significant. It's often worth checking if alternative airports offer more suitable fares or schedules.

Related routes

Consider alternative routes from Des Moines

Flights from Des Moines to Amsterdam Flights from Des Moines to Athens Flights from Des Moines to Bangkok Flights from Des Moines to Beijing Flights from Des Moines to Copenhagen Flights from Des Moines to Denver Flights from Des Moines to Dubai Flights from Des Moines to Edinburgh Flights from Des Moines to Frankfurt Flights from Des Moines to Indianapolis Flights from Des Moines to Las Vegas Flights from Des Moines to Lisbon