Are direct flights from Detroit to Chicago always the best option?

Direct flights are often the most convenient option, saving travel time and reducing the risk of missed connections. However, flights with layovers can sometimes be more economical. Weigh your priorities between cost savings and travel efficiency when making your decision.

Can flexible travel dates help on Detroit to Chicago flights?

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

What extra costs should I check before booking Detroit 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. Factor these into your total travel budget to avoid surprises.

Flights From Detroit

To Chicago

Cheap Flights from Detroit to Chicago

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

Deals from

Detroit

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

Prices updated 7 days ago

482 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 26, 2026.)

Today’s best flight deals from Detroit to Chicago

Explore current cheapest deals departing from Detroit to Chicago

2026-12-09 – 2026-12-15
DTT - Chicago
75% AI deal score
$367
$167
Round trip
2026-12-09 – 2026-12-16
DTT - Chicago
75% AI deal score
$366
$167
Round trip
2026-12-07 – 2026-12-09
DTT - Chicago
75% AI deal score
$391
$171
Round trip
2026-12-08 – 2026-12-16
DTT - Chicago
71% AI deal score
$294
$175
Round trip
2026-12-08 – 2026-12-15
DTT - Chicago
72% AI deal score
$309
$175
Round trip
2026-12-14 – 2026-12-16
DTT - Chicago
75% AI deal score
$391
$176
Round trip
2026-12-07 – 2026-12-15
DTT - Chicago
73% AI deal score
$348
$176
Round trip
2026-12-07 – 2026-12-16
DTT - Chicago
73% AI deal score
$344
$176
Round trip
2027-02-17 – 2027-02-24
DTT - Chicago
41% AI deal score
$188
$176
Round trip
2027-01-05 – 2027-02-03
DTT - Chicago
37% AI deal score
$162
$177
Round trip

Detroit to Chicago: Overview

Insights for flights from Detroit to Chicago

For cheap flights from Detroit to Chicago, fares typically range from $404–$900, with a median of $646. Right now, current fares are above the typical level. Unfortunately, recent fares classified as a good price are 0% of the total.

A typical journey from Detroit to Chicago takes about 1h 37m. However, since most itineraries connect at least once, the median connecting journey time is significantly longer. The route is considered a short-haul flight, covering a distance of 367 kilometers.

When is the cheapest time to fly from Detroit to Chicago? The most affordable month to fly is typically April, with a median fare of $138. Other cost-effective months include February, with a median of $286, and January, where the median fare is $287.

For direct flights from Detroit to Chicago, only 18.3% of recent fares are non-stop. This means most itineraries connect at least once, with a typical connecting flight involving 2 stopovers.

How much is a round trip from Detroit to Chicago

Regular price: $141 - $240

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

The regular price range for flights from Detroit to Chicago is between $141 and $240. The current lowest deal is $156 with Frontier Airlines for travel from Jan 7-Jan 20.

now $156

Low $141

High $240

The cheapest time to fly from Detroit to Chicago

The cheapest month to fly from DTT to CHI is April, with a median price of $138. The most expensive month is December, with a median price of $908. Prices are generally lower from January to November.

April

Cheapest

Flights from $138

December

Most Expensive

Flights from $908

Jan

Feb

Mar

Apr

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Detroit to Chicago

United Airlines

Last-minute flights going from Detroit to Chicago

Tue, Oct 27

⌛ Last-Minute

DTW - Chicago

Detroit (DTW) - Chicago (ORD)

Frontier Airlines

$381

$358

One-way

Tue, Oct 27

⌛ Last-Minute

DTW - Chicago

Detroit (DTW) - Chicago (ORD)

Frontier Airlines

$382

$374

One-way

Wed, Oct 28

⌛ Last-Minute

DTW - Chicago

Detroit (DTW) - Chicago (MDW)

Frontier Airlines

$452

$275

One-way

Mon, Nov 9

⌛ Last-Minute

DTW - Chicago

Detroit (DTW) - Chicago (MDW)

Frontier Airlines

$277

$263

One-way

Tue, Nov 10

⌛ Last-Minute

DTW - Chicago

Detroit (DTW) - Chicago (MDW)

Frontier Airlines

$261

$240

One-way

Tue, Nov 10

⌛ Last-Minute

DTW - Chicago

Detroit (DTW) - Chicago (ORD)

Frontier Airlines

$224

$250

One-way

Biggest price drops on these dates for flights from Detroit to Chicago

1 night

Oct 28 - Oct 29

$460 → $368

20%

2 nights

Oct 27 - Oct 29

$254 → $511

101%

Popular Airports to fly from Detroit to Chicago

Detroit - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Detroit to Chicago are above the typical level, with a median price of $646.

📅 Best time to fly

April is historically the cheapest month to fly

Historically, April is the cheapest month to fly from Detroit to Chicago, with a median price of $138.

⏱️ Flight duration

Direct flights average 1h 37m

Direct flights from Detroit to Chicago typically average 1 hour 37 minutes, while connecting flights average 50 hours 6 minutes.

✈️ Airlines & availability

Connecting flights are dominant on this route

Connecting flights make up 81.7% of options, with a median of 2 stopovers when connecting.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines has offered direct flights on the Detroit to Chicago route.

🎯 Booking tip

Deals appear regularly on this route

This route typically sees deals appear regularly, with a recent deal for $156 on Frontier Airlines.

Detroit main airports to depart from

Detroit Metropolitan (DTW)

Cheapest

Detroit Metropolitan is a good option for flights from Detroit to Chicago, offering competitive pricing.

📍 ~29 km from Detroit (reachable by car)

💸 Flights from ~$190

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a good option for flights from Detroit to Chicago.

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

💸 Flights from ~$146

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

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

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

💸 Flights from ~$320

Business & First Class Flight Deals to Chicago

67% AI deal score

$3,678

$2,226

Save $1,452

Alaska Airlines, Inc.

Business Class

From DTW

Elite

Mar 31

Chicago, United States

67% AI deal score

$3,698

$2,230

Save $1,468

Alaska Airlines, Inc.

Business Class

From DTW

Elite

Mar 31

Chicago, United States

67% AI deal score

$3,717

$2,237

Save $1,480

Alaska Airlines, Inc.

Business Class

From DTW

Elite

Mar 31

Chicago, United States

67% AI deal score

$3,695

$2,237

Save $1,458

Alaska Airlines, Inc.

Business Class

From DTW

Elite

Mar 31

Chicago, United States

67% AI deal score

$3,748

$2,237

Save $1,511

Alaska Airlines, Inc.

Business Class

From DTW

Elite

Mar 31

Chicago, United States

67% AI deal score

$3,702

$2,237

Save $1,465

Alaska Airlines, Inc.

Business Class

From DTW

Elite

Mar 31

Chicago, United States

67% AI deal score

$3,712

$2,269

Save $1,443

Alaska Airlines, Inc.

Business Class

From DTW

Elite

Dec 03

Chicago, United States

66% AI deal score

$3,150

$1,968

Save $1,182

Alaska Airlines, Inc.

Business Class

From DTW

Elite

Dec 03

Chicago, United States

66% AI deal score

$3,142

$1,968

Save $1,174

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

To find potentially cheaper flights, consider being flexible with your travel dates and times. Comparing prices across various airlines and booking platforms can often reveal better deals. Looking into flights during the off-peak season may also help reduce costs.

Booking flights in advance, often several weeks or months before your intended travel date, can sometimes result in lower prices. However, last-minute deals can occasionally appear, so it's wise to monitor price trends. Mid-week bookings may also offer better rates than weekend purchases.

Comparing nearby airports for both your origin and destination can sometimes lead to more affordable flight options. While it may add to your ground transportation, the savings on airfare could be significant. Always factor in the total cost and convenience when considering this approach.

Related routes

More routes from Detroit

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Flights to Chicago from other cities

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Detroit to Chicago: Overview

Insights for flights from Detroit to Chicago

For direct flights from Detroit to Chicago, only 18.3% of recent fares are non-stop. This means most itineraries connect at least once, with a typical connecting flight involving 2 stopovers.

How much is a round trip from Detroit to Chicago

Regular price: $141 - $240

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

The regular price range for flights from Detroit to Chicago is between $141 and $240. The current lowest deal is $156 with Frontier Airlines for travel from Jan 7-Jan 20.

now $156

Low $141

High $240

The cheapest time to fly from Detroit to Chicago

April

Cheapest

Flights from $138

December

Most Expensive

Flights from $908

Jan

Feb

Mar

Apr

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Detroit to Chicago

United Airlines

Last-minute flights going from Detroit to Chicago

Tue, Oct 27

⌛ Last-Minute

DTW - Chicago

Detroit (DTW) - Chicago (ORD)

Frontier Airlines

$381

$358

One-way

Tue, Oct 27

⌛ Last-Minute

DTW - Chicago

Detroit (DTW) - Chicago (ORD)

Frontier Airlines

$382

$374

One-way

Wed, Oct 28

⌛ Last-Minute

DTW - Chicago

Detroit (DTW) - Chicago (MDW)

Frontier Airlines

$452

$275

One-way

Mon, Nov 9

⌛ Last-Minute

DTW - Chicago

Detroit (DTW) - Chicago (MDW)

Frontier Airlines

$277

$263

One-way

Tue, Nov 10

⌛ Last-Minute

DTW - Chicago

Detroit (DTW) - Chicago (MDW)

Frontier Airlines

$261

$240

One-way

Tue, Nov 10

⌛ Last-Minute

DTW - Chicago

Detroit (DTW) - Chicago (ORD)

Frontier Airlines

$224

$250

One-way

Biggest price drops on these dates for flights from Detroit to Chicago

1 night

Oct 28 - Oct 29

$460 → $368

20%

2 nights

Oct 27 - Oct 29

$254 → $511

101%

Popular Airports to fly from Detroit to Chicago

Detroit - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Detroit to Chicago are above the typical level, with a median price of $646.

📅 Best time to fly

April is historically the cheapest month to fly

Historically, April is the cheapest month to fly from Detroit to Chicago, with a median price of $138.

⏱️ Flight duration

Direct flights average 1h 37m

Direct flights from Detroit to Chicago typically average 1 hour 37 minutes, while connecting flights average 50 hours 6 minutes.

✈️ Airlines & availability

Connecting flights are dominant on this route

Connecting flights make up 81.7% of options, with a median of 2 stopovers when connecting.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines has offered direct flights on the Detroit to Chicago route.

🎯 Booking tip

Deals appear regularly on this route

This route typically sees deals appear regularly, with a recent deal for $156 on Frontier Airlines.

Detroit main airports to depart from

Detroit Metropolitan (DTW)

Cheapest

Detroit Metropolitan is a good option for flights from Detroit to Chicago, offering competitive pricing.

📍 ~29 km from Detroit (reachable by car)

💸 Flights from ~$190

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a good option for flights from Detroit to Chicago.

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

💸 Flights from ~$146

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

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

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

💸 Flights from ~$320

Chicago, United States

66% AI deal score

$3,142

$1,968

Save $1,174

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Detroit to Chicago

Today’s best flight deals from Detroit to Chicago

Detroit to Chicago: Overview

Insights for flights from Detroit to Chicago

How much is a round trip from Detroit to Chicago

The cheapest time to fly from Detroit to Chicago

Direct flights from Detroit to Chicago

Last-minute flights going from Detroit to Chicago

Biggest price drops on these dates for flights from Detroit to Chicago

Popular Airports to fly from Detroit to Chicago

Detroit - Chicago route insights

Recent fares are above the typical level

April is historically the cheapest month to fly

Direct flights average 1h 37m

Connecting flights are dominant on this route

United Airlines offers direct flights

Deals appear regularly on this route

Detroit 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

Oct 27

Nov 03

Nov 03

Mar 31

Mar 31

Mar 31

Mar 31

Mar 31

Mar 31

Mar 31

Dec 03

Dec 03

Frequently Asked Questions About Flights to Chicago

How can I find cheap flights from Detroit to Chicago?

When should I book flights from Detroit to Chicago?

Should I compare nearby airports for flights from Detroit to Chicago?

Are direct flights from Detroit to Chicago always the best option?

Can flexible travel dates help on Detroit to Chicago flights?

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

Related routes

More routes from Detroit

Flights to Chicago from other cities

Detroit to Chicago: Overview

Insights for flights from Detroit to Chicago

How much is a round trip from Detroit to Chicago

The cheapest time to fly from Detroit to Chicago

Direct flights from Detroit to Chicago

Last-minute flights going from Detroit to Chicago

Biggest price drops on these dates for flights from Detroit to Chicago

Popular Airports to fly from Detroit to Chicago

Detroit - Chicago route insights

Recent fares are above the typical level

April is historically the cheapest month to fly

Direct flights average 1h 37m

Connecting flights are dominant on this route

United Airlines offers direct flights

Deals appear regularly on this route

Detroit 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

Oct 27

Nov 03

Nov 03

Mar 31

Mar 31

Mar 31

Mar 31

Mar 31

Mar 31

Mar 31

Dec 03

Dec 03

Frequently Asked Questions About Flights to Chicago

How can I find cheap flights from Detroit to Chicago?

When should I book flights from Detroit to Chicago?

Should I compare nearby airports for flights from Detroit to Chicago?