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

Direct flights offer convenience by reducing travel time and avoiding layovers. However, flights with connections can sometimes be more economical. Weighing the cost savings against the added travel time is often a good approach.

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 usually results in lower fares. Adjusting your departure or return by a few days may unlock better deals.

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

Always review 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. Factoring these into your budget can prevent surprises.

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 4 days ago

476 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Oct 12, 2026.)

Today’s best flight deals from Des Moines to Chicago

Explore current cheapest deals departing from Des Moines to Chicago

2026-11-05 – 2026-11-09
DSM - Chicago
41% AI deal score
$190
$240
Round trip
2026-11-19 – 2026-11-26
DSM - Chicago
41% AI deal score
$181
$240
Round trip
2026-11-13 – 2026-11-17
DSM - Chicago
40% AI deal score
$188
$274
Round trip
2026-11-13 – 2026-11-16
DSM - Chicago
40% AI deal score
$188
$274
Round trip
2026-11-21 – 2026-11-22
DSM - Chicago
41% AI deal score
$195
$277
Round trip
2026-11-12 – 2026-12-03
DSM - Chicago
40% AI deal score
$280
$282
Round trip
2026-10-28 – 2026-10-30
DSM - Chicago
40% AI deal score
$217
$294
Round trip
2026-11-12 – 2026-12-06
DSM - Chicago
39% AI deal score
$280
$296
Round trip
2026-11-01 – 2026-11-04
DSM - Chicago
45% AI deal score
$350
$301
Round trip
2026-11-12 – 2026-12-09
DSM - Chicago
39% AI deal score
$280
$302
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 km, classifying this as a short-haul route. This means you can expect a relatively quick journey, often with multiple flight options available.

For those looking for cheap flights from Des Moines to Chicago, fares typically range from $300–$497, with a median price of $311. Right now, fares are below the typical level, and about 9% of recent fares were classified as a good price.

When is the cheapest time to fly from Des Moines to Chicago? The most affordable months to fly are typically November, with a median fare of $300, followed by December at $303, and September at $307. Planning your trip during these months could help you find better value.

A meaningful share of itineraries are non-stop, with 52.4% 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.

The typical journey from Des Moines to Chicago takes 1h 41m, including connections. This duration accounts for both direct flights and those with layovers, providing a comprehensive view of the travel time you can expect.

How much is a round trip from Des Moines to Chicago

Regular price: $238 - $499

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

Regular prices for flights from Des Moines to Chicago typically range from $238 to $499. The current lowest deal is $233 with Frontier Airlines, for travel from Nov 16-Dec 10.

now $233

Low $238

High $499

The cheapest time to fly from Des Moines to Chicago

The cheapest month to fly from Des Moines to Chicago is November, with a median price of $300. The most expensive month is August, with a median price of $497. Generally, prices are lower from January to December, specifically in January, September, November, and December.

November

Cheapest

Flights from $300

August

Most Expensive

Flights from $497

Jan

Feb

Aug

Sep

Oct

Nov

Dec

Direct flights from Des Moines to Chicago

United Airlines

Last-minute flights going from Des Moines to Chicago

Mon, Oct 12

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

United Airlines

$236

$481

One-way

Mon, Oct 12

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

United Airlines

$236

$481

One-way

Sat, Oct 17

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

United Airlines

$203

$492

One-way

Sat, Oct 17

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

United Airlines

$293

$657

One-way

Tue, Oct 20

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

United Airlines

$255

$620

One-way

Tue, Oct 20

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

United Airlines

$257

$620

One-way

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

3 nights

Dec 3 - Dec 6

$376 → $276

27%

17 nights

Nov 16 - Dec 3

$283 → $215

24%

24 nights

Nov 16 - Dec 10

$280 → $247

12%

20 nights

Nov 16 - Dec 6

$280 → $247

12%

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 $233.

📅 Best time to fly

Fly in November for the best prices

Historically, November, December, and September offer the lowest median prices for this route.

⏱️ Flight duration

Direct flights take 1h 41m

Direct flights to Chicago typically take 1 hour 41 minutes, while connecting flights average 22 hours 13 minutes.

✈️ Airlines & availability

52.4% of recent flights are direct

Over half of recent flights from Des Moines to Chicago are direct, offering a mixed selection.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines has direct flights available for the Des Moines to Chicago route.

🎯 Booking tip

Deals are rare for this route

Deals for flights from Des Moines to Chicago are historically rare, so book when you see a good price.

Des Moines main airports to depart from

Des Moines International (DSM)

Cheapest

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

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

💸 Flights from ~$237

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering many flight options to Chicago from Des Moines.

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

💸 Flights from ~$203

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Cheapest

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

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

💸 Flights from ~$294

Business & First Class Flight Deals to Chicago

41% AI deal score

$2,207

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 platforms can often reveal better deals. Setting up price alerts may also help you catch drops in fares.

Booking in advance can often secure better prices, though the ideal booking window can vary. Sometimes, last-minute deals may appear, but this is less common. Monitoring price trends can help you decide when to book.

Comparing nearby airports at both your origin and destination can sometimes lead to more affordable flight options. Even if an airport is further away, the savings on airfare might outweigh the additional ground transportation costs. It's always a good idea to check.

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

How much is a round trip from Des Moines to Chicago

Regular price: $238 - $499

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

Regular prices for flights from Des Moines to Chicago typically range from $238 to $499. The current lowest deal is $233 with Frontier Airlines, for travel from Nov 16-Dec 10.

now $233

Low $238

High $499

The cheapest time to fly from Des Moines to Chicago

November

Cheapest

Flights from $300

August

Most Expensive

Flights from $497

Jan

Feb

Aug

Sep

Oct

Nov

Dec

Direct flights from Des Moines to Chicago

United Airlines

Last-minute flights going from Des Moines to Chicago

Mon, Oct 12

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

United Airlines

$236

$481

One-way

Mon, Oct 12

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

United Airlines

$236

$481

One-way

Sat, Oct 17

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

United Airlines

$203

$492

One-way

Sat, Oct 17

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

United Airlines

$293

$657

One-way

Tue, Oct 20

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

United Airlines

$255

$620

One-way

Tue, Oct 20

⌛ Last-Minute

DSM - Chicago

Des Moines (DSM) - Chicago (ORD)

United Airlines

$257

$620

One-way

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

3 nights

Dec 3 - Dec 6

$376 → $276

27%

17 nights

Nov 16 - Dec 3

$283 → $215

24%

24 nights

Nov 16 - Dec 10

$280 → $247

12%

20 nights

Nov 16 - Dec 6

$280 → $247

12%

Popular Airports to fly from Des Moines to Chicago