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

In the trailing 90 days, approximately 14.1% of flights from Chicago to Guadalajara were non-stop. For flights that include stopovers, travelers typically experience two connections. This indicates that the majority of routes between these two cities involve at least one stop.

How long is the flight from Chicago to Guadalajara?

The direct flight from Chicago to Guadalajara typically takes around 4 hours and 14 minutes, covering a distance of 2789 kilometers. Flights with one stop, however, have a significantly longer median duration, averaging 12 hours and 25 minutes. This difference highlights the convenience of direct routes for this journey.

How often do cheap flights from Chicago to Guadalajara come up?

Historically, cheap flights from Chicago to Guadalajara are a frequent occurrence. This route is classified as offering deals often. Travelers can typically find favorable prices with regularity across the trailing quarter.

Flights From Chicago

To Guadalajara

Cheap Flights from Chicago to Guadalajara

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

Deals from

Chicago

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

Prices updated 7 days ago

483 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 Chicago to Guadalajara

Explore current cheapest deals departing from Chicago to Guadalajara

2027-01-17 – 2027-02-04
CHI - Guadalajara
65% AI deal score
$233
$263
Round trip
2027-01-25 – 2027-02-04
CHI - Guadalajara
65% AI deal score
$244
$265
Round trip
2027-01-20 – 2027-02-04
CHI - Guadalajara
65% AI deal score
$236
$265
Round trip
2027-01-22 – 2027-02-04
CHI - Guadalajara
65% AI deal score
$239
$265
Round trip
2027-01-21 – 2027-02-04
CHI - Guadalajara
65% AI deal score
$239
$265
Round trip
2027-01-28 – 2027-02-04
CHI - Guadalajara
66% AI deal score
$262
$265
Round trip
2027-01-27 – 2027-02-04
CHI - Guadalajara
66% AI deal score
$256
$265
Round trip
2027-01-18 – 2027-02-04
CHI - Guadalajara
65% AI deal score
$233
$265
Round trip
2027-01-19 – 2027-02-04
CHI - Guadalajara
65% AI deal score
$236
$265
Round trip
2027-01-26 – 2027-02-04
CHI - Guadalajara
66% AI deal score
$254
$265
Round trip

Chicago to Guadalajara: Overview

Insights for flights from Chicago to Guadalajara

A typical journey from Chicago to Guadalajara takes about 4h 14m, including connections. This duration accounts for the fact that most itineraries connect at least once, with connecting flights typically involving 2 stopovers. For those seeking direct flights from Chicago to Guadalajara, they represent a smaller portion of available options, with the median connecting flight time extending to 18h 50m.

For travelers looking for cheap flights from Chicago to Guadalajara, prices typically range from $411–$752, with a median of $556. Right now, current fares are above the typical level. Only 3% of recent fares were classified as a good price, indicating that finding significantly lower prices can be challenging.

When is the cheapest time to fly from Chicago to Guadalajara? The data shows that May is the most affordable month, with a median fare of just $220. Other cost-effective months include September, with a median fare of $347, and August, where the median fare is $355. New deals appear almost daily, suggesting frequent opportunities to find better prices if you monitor fares.

The route from Chicago to Guadalajara covers a distance of 2789 kilometers. This classifies it as a medium-haul journey, meaning you can expect a flight duration that is longer than short domestic hops but shorter than intercontinental travel.

How much is a round trip from Chicago to Guadalajara

Regular price: $283 - $923

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

Regular prices for this route typically range from $283 to $923. The current lowest deal is $294 with Aeroenlaces Nacionales for travel from Nov 14-Nov 18.

now $294

Low $283

High $923

The cheapest time to fly from Chicago to Guadalajara

The cheapest month to fly from Chicago to Guadalajara is May, with a median price of $220. The most expensive month is March, with a median price of $816. Prices are generally lower from April to October.

May

Cheapest

Flights from $220

March

Most Expensive

Flights from $816

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Guadalajara

Volaris

Last-minute flights going from Chicago to Guadalajara

Thu, Oct 29

⌛ Last-Minute

RFD - Guadalajara

Chicago (RFD) - Guadalajara (GDL)

Allegiant Air

$793

$612

One-way

Sun, Nov 1

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$572

$439

One-way

Tue, Nov 3

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$441

$358

One-way

Tue, Nov 3

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$524

$373

One-way

Tue, Nov 3

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$469

$381

One-way

Tue, Nov 3

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$531

$412

One-way

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

1 night

Oct 27 - Oct 28

$558 → $320

43%

2 nights

Oct 27 - Oct 29

$558 → $325

42%

2 nights

Nov 3 - Nov 5

$513 → $299

42%

4 nights

Oct 27 - Oct 31

$549 → $335

39%

Popular Airports to fly from Chicago to Guadalajara

Chicago - Guadalajara route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for flights from Chicago to Guadalajara are above the typical level.

📅 Best time to fly

Fly in May for prices around $220

Historically, May has been the cheapest month to fly, with a median price of $220.

⏱️ Flight duration

Direct flights take 4h 14m

The median flight time for a direct flight from Chicago to Guadalajara is 4 hours and 14 minutes.

✈️ Airlines & availability

Connecting flights are common

About 14.1% of recent flights from Chicago to Guadalajara have been direct.

🏆 Airline highlight

Volaris offers direct flights

Volaris is one airline that has offered direct flights on the Chicago to Guadalajara route.

🎯 Booking tip

Deals appear frequently

Deals for flights from Chicago to Guadalajara have appeared frequently in the last 30 days.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

Depart from O'Hare International for flights to Guadalajara, often with competitive prices.

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

💸 Flights from ~$216

Chicago Midway International (MDW)

Consider Chicago Midway International for another departure option to Guadalajara.

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

💸 Flights from ~$261

Chicago Rockford International (RFD)

Chicago Rockford International offers an alternative departure point for your trip to Guadalajara.

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

💸 Flights from ~$352

Guadalajara main airports to arrive at

Guadalajara International (GDL)

Cheapest

Guadalajara International Airport is a convenient arrival choice for travelers flying to Guadalajara.

📍 ~16 km from Guadalajara (reachable by car)

💸 Flights from ~$216

Airports nearby Guadalajara used as alternative

Del Bajío International (BJX)

This major regional hub offers extensive domestic and international connections, useful as an alternative arrival.

📍 ~190 km from Guadalajara (reachable by car, transit time can vary).

💸 Flights from ~$302

Business & First Class Flight Deals to Guadalajara

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

Elite

Best Elite deals to Guadalajara

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

From ORD

Elite

Apr 13

Guadalajara, Mexico

87% AI deal score

$1,136

$748

Save $388

Aeroméxico

Business Class

From ORD

Elite

Apr 13

Guadalajara, Mexico

86% AI deal score

$1,131

$748

Save $383

Aeroméxico

Business Class

From ORD

Elite

Apr 13

Guadalajara, Mexico

86% AI deal score

$1,129

$748

Save $381

Aeroméxico

Business Class

From ORD

Elite

Jan 10

Guadalajara, Mexico

85% AI deal score

$993

$717

Save $276

Aeroméxico

Business Class

From ORD

Elite

Mar 15

Guadalajara, Mexico

85% AI deal score

$1,097

$747

Save $350

Aeroméxico

Business Class

From ORD

Elite

Feb 01

Guadalajara, Mexico

84% AI deal score

$1,003

$726

Save $277

Aeroméxico

Business Class

From ORD

Elite

Apr 13

Guadalajara, Mexico

83% AI deal score

$1,404

$932

Save $472

Aeroméxico

Business Class

From ORD

Elite

Apr 13

Guadalajara, Mexico

83% AI deal score

$1,404

$932

Save $472

Aeroméxico

Business Class

From ORD

Elite

Apr 13

Guadalajara, Mexico

83% AI deal score

$1,418

$932

Save $486

Aeroméxico

Business Class

From ORD

Elite

Apr 13

Guadalajara, Mexico

82% AI deal score

$1,388

$932

Save $456

Aeroméxico

Business Class

From ORD

Elite

Apr 13

Guadalajara, Mexico

82% AI deal score

$1,386

$932

Save $454

Aeroméxico

Business Class

From ORD

Elite

Apr 13

Guadalajara, Mexico

82% AI deal score

$1,387

$932

Save $455

Aeroméxico

Business Class

Frequently Asked Questions About Flights to Guadalajara

Historically, the optimal booking window for flights from Chicago to Guadalajara is typically 7-13 days before departure. During this period, the average price for a ticket is around $296. Prices tend to be significantly higher for very last-minute bookings, averaging $858 for flights booked 0-6 days out. Conversely, booking too far in advance, such as 28-59 days prior, also sees higher average prices of $671.

Across the trailing quarter, a good price for a flight from Chicago to Guadalajara is considered to be $411 or less. The median price for this route over the same period was $556. Prices exceeding $752 typically fall into the higher end of the spectrum. These figures are based on flight data observed over a 90-day window.

Historically, the cheapest months to fly from Chicago to Guadalajara are May, September, and August. May typically offers the lowest median price at $220. September follows with a median price of $347, and August has a median price of $355. The annual median price for this route is $556, making these months notably more affordable.

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Flights to Guadalajara from other cities

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Chicago to Guadalajara: Overview

Insights for flights from Chicago to Guadalajara

How much is a round trip from Chicago to Guadalajara

Regular price: $283 - $923

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

Regular prices for this route typically range from $283 to $923. The current lowest deal is $294 with Aeroenlaces Nacionales for travel from Nov 14-Nov 18.

now $294

Low $283

High $923

The cheapest time to fly from Chicago to Guadalajara

May

Cheapest

Flights from $220

March

Most Expensive

Flights from $816

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Guadalajara

Volaris

Last-minute flights going from Chicago to Guadalajara

Thu, Oct 29

⌛ Last-Minute

RFD - Guadalajara

Chicago (RFD) - Guadalajara (GDL)

Allegiant Air

$793

$612

One-way

Sun, Nov 1

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$572

$439

One-way

Tue, Nov 3

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$441

$358

One-way

Tue, Nov 3

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$524

$373

One-way

Tue, Nov 3

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$469

$381

One-way

Tue, Nov 3

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$531

$412

One-way

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

1 night

Oct 27 - Oct 28

$558 → $320

43%

2 nights

Oct 27 - Oct 29

$558 → $325

42%

2 nights

Nov 3 - Nov 5

$513 → $299

42%

4 nights

Oct 27 - Oct 31

$549 → $335

39%

Popular Airports to fly from Chicago to Guadalajara

Chicago - Guadalajara route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for flights from Chicago to Guadalajara are above the typical level.

📅 Best time to fly

Fly in May for prices around $220

Historically, May has been the cheapest month to fly, with a median price of $220.

⏱️ Flight duration

Direct flights take 4h 14m

The median flight time for a direct flight from Chicago to Guadalajara is 4 hours and 14 minutes.

✈️ Airlines & availability

Connecting flights are common

About 14.1% of recent flights from Chicago to Guadalajara have been direct.

🏆 Airline highlight

Volaris offers direct flights

Volaris is one airline that has offered direct flights on the Chicago to Guadalajara route.

🎯 Booking tip

Deals appear frequently

Deals for flights from Chicago to Guadalajara have appeared frequently in the last 30 days.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

Depart from O'Hare International for flights to Guadalajara, often with competitive prices.

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

💸 Flights from ~$216

Chicago Midway International (MDW)

Consider Chicago Midway International for another departure option to Guadalajara.

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

💸 Flights from ~$261

Chicago Rockford International (RFD)

Chicago Rockford International offers an alternative departure point for your trip to Guadalajara.

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

💸 Flights from ~$352

Guadalajara main airports to arrive at

Guadalajara International (GDL)

Cheapest

Guadalajara International Airport is a convenient arrival choice for travelers flying to Guadalajara.

📍 ~16 km from Guadalajara (reachable by car)

💸 Flights from ~$216

Airports nearby Guadalajara used as alternative

Del Bajío International (BJX)

This major regional hub offers extensive domestic and international connections, useful as an alternative arrival.

Guadalajara, Mexico

82% AI deal score

$1,387

$932

Save $455

Aeroméxico

Business Class

Frequently Asked Questions About Flights to Guadalajara

Cheap Flights from Chicago to Guadalajara

Today’s best flight deals from Chicago to Guadalajara

Chicago to Guadalajara: Overview

Insights for flights from Chicago to Guadalajara

How much is a round trip from Chicago to Guadalajara

The cheapest time to fly from Chicago to Guadalajara

Direct flights from Chicago to Guadalajara

Last-minute flights going from Chicago to Guadalajara

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

Popular Airports to fly from Chicago to Guadalajara

Chicago - Guadalajara route insights

Recent fares are above the typical level

Fly in May for prices around $220

Direct flights take 4h 14m

Connecting flights are common

Volaris offers direct flights

Deals appear frequently

Chicago main airports to depart from

Guadalajara main airports to arrive at

Airports nearby Guadalajara used as alternative

Business & First Class Flight Deals to Guadalajara

Best Elite deals to Guadalajara

Apr 13

Apr 13

Apr 13

Jan 10

Mar 15

Feb 01

Apr 13

Apr 13

Apr 13

Apr 13

Apr 13

Apr 13

Frequently Asked Questions About Flights to Guadalajara

When should I buy Chicago to Guadalajara tickets?

What is a good price for a flight from Chicago to Guadalajara?

When is the cheapest time of year to fly from Chicago to Guadalajara?

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

How long is the flight from Chicago to Guadalajara?

How often do cheap flights from Chicago to Guadalajara come up?

Related routes

More routes from Chicago

Flights to Guadalajara from other cities

Chicago to Guadalajara: Overview

Insights for flights from Chicago to Guadalajara

How much is a round trip from Chicago to Guadalajara

The cheapest time to fly from Chicago to Guadalajara

Direct flights from Chicago to Guadalajara

Last-minute flights going from Chicago to Guadalajara

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

Popular Airports to fly from Chicago to Guadalajara

Chicago - Guadalajara route insights

Recent fares are above the typical level

Fly in May for prices around $220

Direct flights take 4h 14m

Connecting flights are common

Volaris offers direct flights

Deals appear frequently

Chicago main airports to depart from

Guadalajara main airports to arrive at

Airports nearby Guadalajara used as alternative

Business & First Class Flight Deals to Guadalajara

Best Elite deals to Guadalajara

Apr 13

Apr 13

Apr 13

Jan 10

Mar 15

Feb 01

Apr 13

Apr 13

Apr 13

Apr 13

Apr 13

Apr 13

Frequently Asked Questions About Flights to Guadalajara

When should I buy Chicago to Guadalajara tickets?

What is a good price for a flight from Chicago to Guadalajara?

When is the cheapest time of year to fly from Chicago to Guadalajara?