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

In the trailing 90 days, approximately 38.6% of flights from Chicago to Guadalajara were non-stop. For routes that include stopovers, travelers typically experience a median of 2 stopovers. This indicates that while direct options are available, connecting flights are also a common occurrence on this route.

How long is the flight from Chicago to Guadalajara?

The typical direct flight from Chicago to Guadalajara has a duration of 4 hours and 10 minutes, covering a distance of 2789 kilometers. Flights with one stop, however, are significantly longer, with a median duration of 15 hours and 57 minutes. Travelers should consider these differences when planning their journey.

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

Historically, cheap flights from Chicago to Guadalajara come up frequently. This route is classified as one where deals appear with regularity. Travelers looking for budget-friendly options can often find them 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 1 day ago

461 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Chicago to Guadalajara

Explore current cheapest deals departing from Chicago to Guadalajara

2026-10-26 – 2026-10-30
CHI - Guadalajara
77% AI deal score
$288
$238
Round trip
2026-10-26 – 2026-10-28
CHI - Guadalajara
77% AI deal score
$289
$238
Round trip
2026-11-08 – 2026-11-17
CHI - Guadalajara
79% AI deal score
$306
$238
Round trip
2026-11-08 – 2026-11-18
CHI - Guadalajara
78% AI deal score
$294
$238
Round trip
2026-11-08 – 2026-11-19
CHI - Guadalajara
77% AI deal score
$290
$238
Round trip
2026-11-08 – 2026-11-20
CHI - Guadalajara
77% AI deal score
$288
$238
Round trip
2026-11-08 – 2026-11-10
CHI - Guadalajara
80% AI deal score
$331
$238
Round trip
2026-10-26 – 2026-11-10
CHI - Guadalajara
67% AI deal score
$242
$238
Round trip
2026-10-26 – 2026-11-19
CHI - Guadalajara
66% AI deal score
$237
$238
Round trip
2026-10-26 – 2026-11-18
CHI - Guadalajara
66% AI deal score
$238
$238
Round trip

Chicago to Guadalajara: Overview

Insights for flights from Chicago to Guadalajara

A typical journey from Chicago to Guadalajara takes about 4h 10m, including connections. Given that most itineraries connect at least once, this median duration reflects the overall travel time you can expect. For direct flights from Chicago to Guadalajara, the flight time is also around 4h 10m, while connecting flights typically extend to 15h 57m.

For travelers seeking cheap flights from Chicago to Guadalajara, prices typically range from $283–$665, with a median of $439. Right now, fares are below the typical level. Approximately 20% of recent fares from Chicago to Guadalajara have been classified as a good price, indicating opportunities for savings.

When is the cheapest time to fly from Chicago to Guadalajara? The data indicates that March is often the most affordable month, with a median fare of $145. Other cost-effective options include January, with a median fare of $178, and February, where the median fare is $190.

Most itineraries from Chicago to Guadalajara connect at least once, with only 38.6% of recent fares being non-stop. For those flights that do include connections, the typical number of stopovers is 2. New deals for this route appear almost daily, offering frequent opportunities to find favorable prices.

The distance between Chicago and Guadalajara is 2789 kilometers. This classifies the route as a medium-haul journey, meaning you can expect a flight that is neither extremely short nor a full long-distance international trip.

How much is a round trip from Chicago to Guadalajara

Regular price: $400 - $600

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

The regular price range for this route is typically between $400 and $600. The current lowest deal is $297 with Aeroenlaces Nacionales for travel from Sep 27-Sep 29.

now $297

Low $400

High $600

The cheapest time to fly from Chicago to Guadalajara

The cheapest month to fly from Chicago to Guadalajara is January, with a median price of $246. The most expensive month is December, with a median price of $867. Prices are generally lower from January to October.

January

Cheapest

Flights from $246

December

Most Expensive

Flights from $867

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

Tue, Sep 15

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Volaris

$637

$377

One-way

Wed, Sep 16

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$529

$303

One-way

Wed, Sep 16

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$637

$363

One-way

Wed, Sep 16

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$640

$366

One-way

Mon, Sep 21

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$559

$326

One-way

Sun, Sep 27

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$488

$297

One-way

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

3 nights

Sep 20 - Sep 23

$716 → $390

46%

3 nights

Sep 15 - Sep 18

$629 → $340

46%

2 nights

Sep 14 - Sep 16

$637 → $360

44%

2 nights

Sep 15 - Sep 17

$637 → $380

40%

Popular Airports to fly from Chicago to Guadalajara

Chicago - Guadalajara route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Chicago to Guadalajara are below the typical level, with 20% considered good deals.

📅 Best time to fly

Fly in March for the lowest prices

Historically, March offers the lowest median prices at $145, followed by January and February.

⏱️ Flight duration

Direct flights take 4h 10m

Direct flights typically take 4h 10m, while connecting flights average 15h 57m.

✈️ Airlines & availability

Connecting flights are more common

Connecting flights make up 61.4% of routes, with a median of 2 stopovers.

🏆 Airline highlight

Volaris offers direct flights

Volaris is an airline that offers direct flights from Chicago to Guadalajara.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Chicago to Guadalajara are frequent, appearing within a 30-day window.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

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

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

💸 Flights from ~$236

Chicago Midway International (MDW)

Consider Chicago Midway International Airport for a convenient departure point to Guadalajara.

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

💸 Flights from ~$286

Chicago Rockford International (RFD)

Chicago Rockford International Airport is an alternative departure option for your trip to Guadalajara.

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

💸 Flights from ~$418

Guadalajara main airports to arrive at

Guadalajara International (GDL)

Cheapest

Guadalajara International Airport is a convenient arrival point for flights from Chicago to Guadalajara.

📍 ~16 km from Guadalajara (reachable by car)

💸 Flights from ~$237

Airports nearby Guadalajara used as alternative

Del Bajío International (BJX)

This major regional hub offers extensive domestic and international connections, serving as a strong alternative.

📍 ~240 km from Guadalajara (reachable by car, but ground transit time can vary).

💸 Flights from ~$264

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

Dec 09

Guadalajara, Mexico

89% AI deal score

$1,354

$691

Save $663

United Airlines

Business Class

From ORD

Elite

Dec 26

Guadalajara, Mexico

89% AI deal score

$1,406

$711

Save $695

United Airlines

Business Class

From ORD

Elite

Mar 04

Guadalajara, Mexico

88% AI deal score

$1,336

$731

Save $605

United Airlines

Business Class

From ORD

Elite

Dec 11

Guadalajara, Mexico

88% AI deal score

$1,394

$745

Save $649

United Airlines

Business Class

From ORD

Elite

Dec 30

Guadalajara, Mexico

88% AI deal score

$1,451

$765

Save $686

United Airlines

Business Class

From ORD

Elite

Jan 11

Guadalajara, Mexico

87% AI deal score

$1,283

$711

Save $572

United Airlines

Business Class

From ORD

Elite

Nov 11

Guadalajara, Mexico

87% AI deal score

$1,349

$736

Save $613

United Airlines

Business Class

From ORD

Elite

Dec 07

Guadalajara, Mexico

87% AI deal score

$1,349

$745

Save $604

United Airlines

Business Class

From ORD

Elite

Dec 05

Guadalajara, Mexico

87% AI deal score

$1,342

$745

Save $597

United Airlines

Business Class

From ORD

Elite

Dec 04

Guadalajara, Mexico

87% AI deal score

$1,342

$745

Save $597

United Airlines

Business Class

From ORD

Elite

Dec 11

Guadalajara, Mexico

87% AI deal score

$1,358

$765

Save $593

United Airlines

Business Class

From ORD

Elite

Dec 07

Guadalajara, Mexico

87% AI deal score

$1,349

$765

Save $584

United Airlines

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 observed was $301. Prices tend to be higher if booked too far in advance, with flights booked 28-59 days out averaging $520. Conversely, waiting until 0-6 days before departure can see prices rise significantly, with an average of $603.

Across the trailing quarter, a good price for a flight from Chicago to Guadalajara is considered to be $283 or less. The median price for this route historically stands at $439. Prices can range significantly, with 75% of observed prices being $665 or less.

Historically, the cheapest months to fly from Chicago to Guadalajara are March, January, and February. In March, the median price was $145, while January saw a median of $178. February also offered competitive prices with a median of $190. These months are significantly cheaper than the annual median price of $439 for this route.

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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: $400 - $600

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

The regular price range for this route is typically between $400 and $600. The current lowest deal is $297 with Aeroenlaces Nacionales for travel from Sep 27-Sep 29.

now $297

Low $400

High $600

The cheapest time to fly from Chicago to Guadalajara

January

Cheapest

Flights from $246

December

Most Expensive

Flights from $867

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

Tue, Sep 15

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Volaris

$637

$377

One-way

Wed, Sep 16

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$529

$303

One-way

Wed, Sep 16

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$637

$363

One-way

Wed, Sep 16

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$640

$366

One-way

Mon, Sep 21

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$559

$326

One-way

Sun, Sep 27

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$488

$297

One-way

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

3 nights

Sep 20 - Sep 23

$716 → $390

46%

3 nights

Sep 15 - Sep 18

$629 → $340

46%

2 nights

Sep 14 - Sep 16

$637 → $360

44%

2 nights

Sep 15 - Sep 17

$637 → $380

40%

Popular Airports to fly from Chicago to Guadalajara

Chicago - Guadalajara route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Chicago to Guadalajara are below the typical level, with 20% considered good deals.

📅 Best time to fly

Fly in March for the lowest prices

Historically, March offers the lowest median prices at $145, followed by January and February.

⏱️ Flight duration

Direct flights take 4h 10m

Direct flights typically take 4h 10m, while connecting flights average 15h 57m.

✈️ Airlines & availability

Connecting flights are more common

Connecting flights make up 61.4% of routes, with a median of 2 stopovers.

🏆 Airline highlight

Volaris offers direct flights

Volaris is an airline that offers direct flights from Chicago to Guadalajara.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Chicago to Guadalajara are frequent, appearing within a 30-day window.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

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

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

💸 Flights from ~$236

Chicago Midway International (MDW)

Consider Chicago Midway International Airport for a convenient departure point to Guadalajara.

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

💸 Flights from ~$286

Chicago Rockford International (RFD)

Chicago Rockford International Airport is an alternative departure option for your trip to Guadalajara.

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

💸 Flights from ~$418

Guadalajara main airports to arrive at

Guadalajara International (GDL)

Cheapest

Guadalajara International Airport is a convenient arrival point for flights from Chicago to Guadalajara.

📍 ~16 km from Guadalajara (reachable by car)

💸 Flights from ~$237

Airports nearby Guadalajara used as alternative

Del Bajío International (BJX)

This major regional hub offers extensive domestic and international connections, serving as a strong alternative.

Guadalajara, Mexico

87% AI deal score

$1,349

$765

Save $584

United Airlines

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 below the typical level

Fly in March for the lowest prices

Direct flights take 4h 10m

Connecting flights are more common

Volaris offers direct flights

Deals are frequent on this route

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

Dec 09

Dec 26

Mar 04

Dec 11

Dec 30

Jan 11

Nov 11

Dec 07

Dec 05

Dec 04

Dec 11

Dec 07

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 below the typical level

Fly in March for the lowest prices

Direct flights take 4h 10m

Connecting flights are more common

Volaris offers direct flights

Deals are frequent on this route

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

Dec 09

Dec 26

Mar 04

Dec 11

Dec 30

Jan 11

Nov 11

Dec 07

Dec 05

Dec 04

Dec 11

Dec 07

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?