How many flights from Cancún to Chicago are non-stop?

In the trailing 90 days, approximately 17.8% of flights from Cancún to Chicago have been non-stop. The majority of flights on this route involve at least one stopover. For flights with connections, the median number of stopovers has historically been 2. Travelers prioritizing direct routes should consider this percentage when planning their journey.

How long does it take to fly from Cancún to Chicago?

The typical direct flight from Cancún to Chicago has a median duration of 4 hours and 7 minutes. This covers an approximate distance of 2309 kilometers. Flights with one stopover, however, take considerably longer, with a median duration of 8 hours and 49 minutes. Travelers should account for these differences in flight time when making their travel plans.

Should I set a price alert for Cancún to Chicago flights?

Based on historical trends, flights from Cancún to Chicago are classified as a frequent deal route. This indicates that price fluctuations and opportunities for savings occur regularly. Setting a price alert can be beneficial for this route, as it allows travelers to be notified when prices drop. This can help in securing a more favorable fare for the journey.

Flights From Cancún

To Chicago

Cheap Flights from Cancún to Chicago

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

Deals from

Cancún

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

Prices updated 6 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 19, 2026.)

Today’s best flight deals from Cancún to Chicago

Explore current cheapest deals departing from Cancún to Chicago

Round trip

Sort by: Cheapest

September 3 - September 7

Cheapest

CUN - Chicago

$358

$255

Round trip

September 3 - September 8

CUN - Chicago

$353

$267

Round trip

August 25 - August 28

Best

Earliest

CUN - Chicago

$433

$278

Round trip

September 23 - September 28

CUN - Chicago

$358

$280

Round trip

September 22 - September 29

CUN - Chicago

$350

$280

Round trip

September 3 - October 3

CUN - Chicago

$301

$281

Round trip

September 24 - October 3

CUN - Chicago

$337

$281

Round trip

September 17 - October 3

CUN - Chicago

$315

$281

Round trip

September 25 - September 29

CUN - Chicago

$358

$282

Round trip

January 22 - January 25

CUN - Chicago

$383

$282

Round trip

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

Cancún to Chicago: Overview

Insights for flights from Cancún to Chicago

Flights from Cancún to Chicago typically range from $343–$657, with a median fare of $464. Right now, fares for this route are above the typical level, and only 1% of recent fares were classified as a good price. New deals appear almost daily, suggesting frequent opportunities to find cheap flights from Cancún to Chicago.

For travelers wondering when is the cheapest time to fly from Cancún to Chicago, the data indicates that January is typically the most affordable month, with a median fare of $162. Other cost-effective months include March, with a median of $227, and April, where the median fare is $248.

A typical journey from Cancún to Chicago takes approximately 11h 20m, including connections. This is largely due to the nature of itineraries on this route; most itineraries connect at least once, with a median of 2 stopovers when connecting. Only 17.8% of recent fares were for direct flights from Cancún to Chicago.

The route from Cancún to Chicago covers a distance of 2309 kilometers, classifying it as a medium-haul flight. This distance means that while direct options exist, many travelers will experience connecting flights.

How much is a round trip from Cancún to Chicago

Regular price: $307 - $504

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

The regular price range for this route is between $307 and $504. The current lowest deal is $251 with Maersk Air for travel from Sep 3-Sep 7.

now $251

Low $307

High $504

The cheapest time to fly from Cancún to Chicago

The cheapest month to fly from Cancun to Chicago is January, with a median price of $162. The most expensive month is October, with a median price of $737. Prices are generally lower from January to December.

January

Cheapest

Flights from $162

October

Most Expensive

Flights from $737

Jan

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Cancún to Chicago

Southwest Airlines

United Airlines

Last-minute flights going from Cancún to Chicago

Thu, Jul 16

⌛ Last-Minute

CUN - Chicago

Cancún (CUN) - Chicago (ORD)

Volaris

$437

$319

One-way

Sat, Jul 18

⌛ Last-Minute

CUN - Chicago

Cancún (CUN) - Chicago (ORD)

Volaris

$414

$317

One-way

Sat, Aug 15

⌛ Last-Minute

CUN - Chicago

Cancún (CUN) - Chicago (ORD)

Volaris

$413

$314

One-way

Thu, Aug 20

⌛ Last-Minute

CUN - Chicago

Cancún (CUN) - Chicago (ORD)

Volaris

$423

$311

One-way

Fri, Aug 21

⌛ Last-Minute

CUN - Chicago

Cancún (CUN) - Chicago (ORD)

Volaris

$410

$312

One-way

Fri, Aug 21

⌛ Last-Minute

CUN - Chicago

Cancún (CUN) - Chicago (ORD)

Volaris

$431

$320

One-way

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

4 nights

Jun 18 - Jun 22

$485 → $314

35%

1 night

Jun 20 - Jun 21

$491 → $320

35%

3 nights

Jun 19 - Jun 22

$488 → $335

31%

3 nights

Jun 23 - Jun 26

$466 → $320

31%

Popular Airports to fly from Cancún to Chicago

Cancún - Chicago route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Cancún to Chicago are below the typical level at $251.

📅 Best time to fly

January is historically the cheapest month to fly

Historically, January is the cheapest month to fly, with a median price of $162.

⏱️ Flight duration

Flights are typically 11h 20m connecting

The typical flight duration from Cancún to Chicago is 11h 20m, including stopovers.

✈️ Airlines & availability

Connecting flights are dominant on this route

Connecting flights make up 82.2% of recent deals, with 2 stopovers on average.

🏆 Airline highlight

Maersk Air offers a recent deal for $251

Maersk Air recently offered a flight for $251 from Cancún to Chicago via skyscanner.

🎯 Booking tip

Deals appear frequently on this route

Deals for flights from Cancún to Chicago appear frequently, typically within a 30-day window.

Cancún main airports to depart from

Cancún International (CUN)

Cheapest

Cancún International offers flights to Chicago, providing a convenient departure point for your trip.

📍 ~15 km from Cancún city center (reachable by car)

💸 Flights from ~$270

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights to Chicago, offering a wide range of connections.

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

💸 Flights from ~$270

Chicago Midway International (MDW)

Chicago Midway International Airport provides convenient access to the city, especially for those traveling from Cancún.

📍 ~15 km from Chicago city center (reachable by car, train, and bus)

💸 Flights from ~$392

Chicago Rockford International (RFD)

Chicago Rockford International Airport is an alternative for travelers heading to the wider Chicago area.

📍 ~120 km from Chicago city center (reachable by car)

💸 Flights from ~$486

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 car or rail)

💸 Flights from ~$481

South Bend International (SBN)

South Bend International is geographically the closest alternative to Chicago, connected via the South Shore Line.

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

💸 Flights from ~$478

Gerald R. Ford International (GRR)

Cheapest

Gerald R. Ford International is a major regional hub, offering a wide range of cabin classes.

📍 ~230 km from Chicago (reachable by car)

💸 Flights from ~$442

Dane County Regional (MSN)

Dane County Regional is a reliable regional airport, less congested than major Chicago or Milwaukee airports.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$468

Fort Wayne International (FWA)

Fort Wayne International provides stable regional service for travelers in the southeastern Chicago suburbs.

📍 ~250 km from Chicago (reachable by car)

💸 Flights from ~$495

Business & First Class Flight Deals to Chicago

Discover luxury on the budget with premium cabin class on flights from Cancún to Chicago.

Elite

Best Elite deals to Chicago

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From CUN

Elite

Aug 12

Chicago, United States

88% AI deal score

$1,573

$807

Save $766

From CUN

Elite

Oct 22

Chicago, United States

86% AI deal score

$1,717

$858

Save $859

From CUN

Elite

Aug 20

Chicago, United States

85% AI deal score

$1,188

$736

Save $452

From CUN

Elite

Jul 23

Chicago, United States

84% AI deal score

$1,245

$747

Save $498

From CUN

Elite

Oct 02

Chicago, United States

83% AI deal score

$1,655

$970

Save $685

From CUN

Elite

Aug 20

Chicago, United States

82% AI deal score

$1,114

$793

Save $321

From CUN

Elite

Jul 13

Chicago, United States

82% AI deal score

$1,189

$793

Save $396

From CUN

Elite

Aug 03

Chicago, United States

82% AI deal score

$1,163

$793

Save $370

From CUN

Elite

Jul 09

Chicago, United States

82% AI deal score

$1,235

$793

Save $442

From CUN

Elite

Jul 22

Chicago, United States

82% AI deal score

$1,225

$806

Save $419

From CUN

Elite

Oct 30

Chicago, United States

82% AI deal score

$1,332

$836

Save $496

From CUN

Elite

Nov 17

Chicago, United States

82% AI deal score

$1,266

$836

Save $430

From CUN

Elite

Nov 05

Chicago, United States

82% AI deal score

$1,268

$836

Save $432

From CUN

Elite

Nov 05

Chicago, United States

82% AI deal score

$1,271

$836

Save $435

From CUN

Elite

Oct 27

Chicago, United States

82% AI deal score

$1,340

$837

Save $503

From CUN

Elite

Oct 27

Chicago, United States

82% AI deal score

$1,339

$837

Save $502

From CUN

Elite

Oct 28

Chicago, United States

82% AI deal score

$1,340

$841

Save $499

From CUN

Elite

Oct 27

Chicago, United States

82% AI deal score

$1,340

$841

Save $499

From CUN

Elite

Oct 28

Chicago, United States

82% AI deal score

$1,340

$841

Save $499

From CUN

Elite

Oct 29

Chicago, United States

82% AI deal score

$1,330

$841

Save $489

From CUN

Elite

Nov 05

Chicago, United States

82% AI deal score

$1,276

$841

Save $435

From CUN

Elite

Oct 30

Chicago, United States

82% AI deal score

$1,331

$841

Save $490

From CUN

Elite

Oct 29

Chicago, United States

82% AI deal score

$1,318

$841

Save $477

From CUN

Elite

Oct 21

Chicago, United States

82% AI deal score

$1,344

$847

Save $497

From CUN

Elite

Oct 16

Chicago, United States

82% AI deal score

$1,344

$847

Save $497

From CUN

Elite

Oct 23

Chicago, United States

82% AI deal score

$1,344

$847

Save $497

From CUN

Elite

Oct 21

Chicago, United States

82% AI deal score

$1,344

$847

Save $497

From CUN

Elite

Oct 13

Chicago, United States

82% AI deal score

$1,344

$847

Save $497

From CUN

Elite

Oct 23

Chicago, United States

82% AI deal score

$1,344

$847

Save $497

From CUN

Elite

Oct 14

Chicago, United States

82% AI deal score

$1,345

$847

Save $498

From CUN

Elite

Oct 22

Chicago, United States

82% AI deal score

$1,344

$847

Save $497

From CUN

Elite

Oct 22

Chicago, United States

82% AI deal score

$1,344

$847

Save $497

From CUN

Elite

Sep 24

Chicago, United States

81% AI deal score

$1,172

$806

Save $366

From CUN

Elite

Jul 29

Chicago, United States

81% AI deal score

$1,170

$806

Save $364

From CUN

Elite

Jul 29

Chicago, United States

81% AI deal score

$1,188

$806

Save $382

From CUN

Elite

Aug 06

Chicago, United States

81% AI deal score

$1,120

$818

Save $302

From CUN

Elite

Jul 24

Chicago, United States

81% AI deal score

$1,183

$818

Save $365

From CUN

Elite

Aug 06

Chicago, United States

81% AI deal score

$1,168

$831

Save $337

From CUN

Elite

Aug 01

Chicago, United States

81% AI deal score

$1,163

$840

Save $323

From CUN

Elite

Nov 13

Chicago, United States

81% AI deal score

$1,256

$836

Save $420

From CUN

Elite

Nov 11

Chicago, United States

81% AI deal score

$1,257

$836

Save $421

From CUN

Elite

Nov 04

Chicago, United States

81% AI deal score

$1,268

$841

Save $427

From CUN

Elite

Nov 04

Chicago, United States

81% AI deal score

$1,271

$841

Save $430

From CUN

Elite

Nov 11

Chicago, United States

81% AI deal score

$1,257

$841

Save $416

From CUN

Elite

Nov 13

Chicago, United States

81% AI deal score

$1,247

$841

Save $406

From CUN

Elite

Nov 03

Chicago, United States

81% AI deal score

$1,276

$847

Save $429

From CUN

Elite

Nov 03

Chicago, United States

81% AI deal score

$1,277

$847

Save $430

From CUN

Elite

Jul 24

Chicago, United States

80% AI deal score

$1,177

$831

Save $346

From CUN

Elite

Jul 22

Chicago, United States

80% AI deal score

$1,171

$831

Save $340

From CUN

Elite

Aug 02

Chicago, United States

80% AI deal score

$1,163

$858

Save $305

From CUN

Elite

Aug 19

Chicago, United States

80% AI deal score

$1,169

$863

Save $306

From CUN

Elite

Sep 16

Chicago, United States

80% AI deal score

$1,314

$895

Save $419

From CUN

Elite

Aug 01

Chicago, United States

79% AI deal score

$1,115

$853

Save $262

From CUN

Elite

Jul 30

Chicago, United States

79% AI deal score

$1,185

$858

Save $327

From CUN

Elite

Jul 15

Chicago, United States

79% AI deal score

$1,187

$858

Save $329

From CUN

Elite

Sep 30

Chicago, United States

75% AI deal score

$1,143

$858

Save $285

From CUN

Elite

Sep 22

Chicago, United States

74% AI deal score

$1,110

$858

Save $252

From CUN

Elite

Jul 19

Chicago, United States

74% AI deal score

$1,179

$900

Save $279

From CUN

Elite

Dec 04

Chicago, United States

74% AI deal score

$1,253

$905

Save $348

From CUN

Elite

Aug 22

Chicago, United States

74% AI deal score

$1,114

$905

Save $209

From CUN

Elite

Aug 21

Chicago, United States

74% AI deal score

$1,114

$905

Save $209

From CUN

Elite

Jul 18

Chicago, United States

74% AI deal score

$1,183

$905

Save $278

From CUN

Elite

Aug 24

Chicago, United States

74% AI deal score

$1,152

$912

Save $240

From CUN

Elite

Jul 16

Chicago, United States

74% AI deal score

$1,187

$918

Save $269

From CUN

Elite

Jul 16

Chicago, United States

74% AI deal score

$1,186

$918

Save $268

From CUN

Elite

Nov 24

Chicago, United States

74% AI deal score

$3,471

$2,565

Save $906

From CUN

Elite

Nov 25

Chicago, United States

74% AI deal score

$3,482

$2,583

Save $899

From CUN

Elite

Nov 24

Chicago, United States

74% AI deal score

$3,471

$2,607

Save $864

From CUN

Elite

Aug 05

Chicago, United States

73% AI deal score

$1,105

$918

Save $187

From CUN

Elite

Nov 24

Chicago, United States

73% AI deal score

$3,297

$2,512

Save $785

From CUN

Elite

Nov 23

Chicago, United States

73% AI deal score

$3,226

$2,576

Save $650

From CUN

Elite

Dec 11

Chicago, United States

73% AI deal score

$3,319

$2,620

Save $699

From CUN

Elite

Nov 25

Chicago, United States

73% AI deal score

$3,474

$2,625

Save $849

From CUN

Elite

Nov 23

Chicago, United States

73% AI deal score

$3,471

$2,629

Save $842

From CUN

Elite

Nov 20

Chicago, United States

73% AI deal score

$3,481

$2,629

Save $852

From CUN

Elite

Nov 22

Chicago, United States

73% AI deal score

$3,471

$2,632

Save $839

From CUN

Elite

Dec 10

Chicago, United States

73% AI deal score

$3,374

$2,654

Save $720

From CUN

Elite

Dec 12

Chicago, United States

73% AI deal score

$3,444

$2,662

Save $782

From CUN

Elite

Nov 20

Chicago, United States

73% AI deal score

$3,459

$2,671

Save $788

From CUN

Elite

Nov 23

Chicago, United States

73% AI deal score

$3,467

$2,671

Save $796

From CUN

Elite

Nov 22

Chicago, United States

73% AI deal score

$3,481

$2,674

Save $807

From CUN

Elite

Nov 21

Chicago, United States

73% AI deal score

$3,467

$2,689

Save $778

From CUN

Elite

Nov 21

Chicago, United States

73% AI deal score

$3,459

$2,731

Save $728

From CUN

Elite

Nov 24

Chicago, United States

72% AI deal score

$3,097

$2,525

Save $572

From CUN

Elite

Nov 25

Chicago, United States

72% AI deal score

$3,099

$2,543

Save $556

From CUN

Elite

Dec 04

Chicago, United States

72% AI deal score

$3,089

$2,577

Save $512

From CUN

Elite

Nov 22

Chicago, United States

72% AI deal score

$3,165

$2,578

Save $587

From CUN

Elite

Nov 23

Chicago, United States

72% AI deal score

$3,117

$2,589

Save $528

From CUN

Elite

Nov 20

Chicago, United States

72% AI deal score

$3,083

$2,589

Save $494

From CUN

Elite

Nov 22

Chicago, United States

72% AI deal score

$3,117

$2,592

Save $525

From CUN

Elite

Dec 04

Chicago, United States

72% AI deal score

$3,109

$2,620

Save $489

From CUN

Elite

Dec 03

Chicago, United States

72% AI deal score

$3,089

$2,620

Save $469

From CUN

Elite

Dec 02

Chicago, United States

72% AI deal score

$3,109

$2,620

Save $489

From CUN

Elite

Nov 21

Chicago, United States

72% AI deal score

$3,093

$2,649

Save $444

From CUN

Elite

Dec 10

Chicago, United States

72% AI deal score

$3,245

$2,696

Save $549

From CUN

Elite

Dec 08

Chicago, United States

72% AI deal score

$3,245

$2,747

Save $498

From CUN

Elite

Dec 09

Chicago, United States

72% AI deal score

$3,300

$2,789

Save $511

From CUN

Elite

Nov 20

Chicago, United States

71% AI deal score

$2,943

$2,576

Save $367

From CUN

Elite

Nov 21

Chicago, United States

71% AI deal score

$3,078

$2,636

Save $442

From CUN

Elite

Dec 03

Chicago, United States

71% AI deal score

$3,109

$2,662

Save $447

Frequently Asked Questions About Flights to Chicago

Historically, the optimal time to purchase tickets for flights from Cancún to Chicago is typically 14-27 days before departure. During this booking window, the average price for a ticket is around $316. Prices tend to be higher for last-minute bookings, with flights purchased 7-13 days out averaging $515. For those planning further ahead, flights booked 28-59 days in advance have an average price of $524.

Across the trailing quarter, a good deal for a flight from Cancún to Chicago is considered to be $343 or less. The median price for this route has historically been around $464. Prices can go significantly higher, with 75% of observed prices being $657 or more. Keeping an eye out for fares at or below the $343 threshold can help secure a favorable price.

Historically, the cheapest months to fly from Cancún to Chicago include January, March, and April. January typically sees a median price of $162, making it the most affordable month. March and April also offer competitive prices, with median fares of $227 and $248 respectively. These prices are significantly lower than the annual median price of $464 for this route.

Related routes

Consider alternative routes from Cancún

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