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 flights that include stopovers, the median number of stopovers observed was 2. This indicates that while direct options are available, a significant portion of the routes involve at least one connection. Travelers should consider this when planning their journey.

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. This represents a substantial difference in travel time, with direct flights being considerably faster.

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 high regularity. Travelers looking for budget-friendly options can expect to find them often when planning their trips. This consistent availability makes it easier to secure favorable pricing for this destination.

Flights From Chicago

To Guadalajara

Cheap Flights from Chicago to Guadalajara

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Deals from

Chicago

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

Prices updated 2 days ago

405 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 26, 2026.)

Today’s best flight deals from Chicago to Guadalajara

Explore current cheapest deals departing from Chicago to Guadalajara

2026-09-01 – 2026-09-10
CHI - Guadalajara
72% AI deal score
$298
$252
Round trip
2026-11-12 – 2026-11-16
CHI - Guadalajara
85% AI deal score
$470
$259
Round trip
2026-11-08 – 2026-11-26
CHI - Guadalajara
76% AI deal score
$317
$261
Round trip
2026-09-01 – 2026-09-04
CHI - Guadalajara
77% AI deal score
$326
$262
Round trip
2026-11-13 – 2026-11-26
CHI - Guadalajara
83% AI deal score
$429
$262
Round trip
2026-11-10 – 2026-11-26
CHI - Guadalajara
82% AI deal score
$410
$264
Round trip
2026-11-07 – 2026-11-26
CHI - Guadalajara
72% AI deal score
$314
$264
Round trip
2026-09-06 – 2026-09-12
CHI - Guadalajara
82% AI deal score
$405
$267
Round trip
2026-11-12 – 2026-11-26
CHI - Guadalajara
83% AI deal score
$426
$267
Round trip
2026-11-06 – 2026-11-26
CHI - Guadalajara
81% AI deal score
$392
$268
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. For itineraries that involve connecting flights, the median travel time extends to 15h 57m. This route is classified as medium-haul, covering a distance of 2789 kilometers.

When looking for cheap flights from Chicago to Guadalajara, you'll find that fares typically range from $283–$665, with a median price of $439. Right now, current fares are below the typical level, and approximately 20% of recent fares were classified as a good price. New deals appear almost daily for this route.

If you are wondering when is the cheapest time to fly from Chicago to Guadalajara, the data indicates that March is typically the most affordable month, with a median fare of $145. January also offers competitive prices, with a median of $178, followed by February at $190.

For flights from Chicago to Guadalajara, most itineraries connect at least once, with only 38.6% of recent fares being non-stop. When a connection is necessary, the typical number of stopovers is 2.

How much is a round trip from Chicago to Guadalajara

Regular price: $264 - $579

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

The regular price range for flights from Chicago to Guadalajara is typically between $264 and $579. The current lowest deal is $252 with Aeroenlaces Nacionales for travel from Sep 1-Sep 10.

now $252

Low $264

High $579

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

Aeroenlaces Nacionales

Last-minute flights going from Chicago to Guadalajara

Thu, Aug 13

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$432

$273

One-way

Sun, Aug 23

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$485

$280

One-way

Sun, Aug 23

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$514

$287

One-way

Mon, Aug 24

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$407

$270

One-way

Mon, Aug 24

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$484

$271

One-way

Mon, Aug 24

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$500

$277

One-way

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

4 nights

Dec 3 - Dec 7

$582 → $300

48%

5 nights

Dec 8 - Dec 13

$589 → $307

48%

3 nights

Dec 8 - Dec 11

$588 → $307

48%

4 nights

Dec 8 - Dec 12

$587 → $307

48%

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 of $439.

📅 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 $246.

⏱️ Flight duration

Direct flights take 4h 10m

Direct flights from Chicago to Guadalajara typically take 4h 10m, while connecting flights take 15h 57m.

✈️ Airlines & availability

Connecting flights are dominant on this route

Connecting flights are dominant, making up 61.4% of recent fares from Chicago to Guadalajara.

🏆 Airline highlight

Aeroenlaces Nacionales offers direct flights

Aeroenlaces Nacionales offers direct flights, with one recent deal found for $252.

🎯 Booking tip

Deals appear frequently on this route

Deals from Chicago to Guadalajara appear frequently, with many deals found 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, offering a convenient option for your journey.

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

💸 Flights from ~$249

Guadalajara main airports to arrive at

Guadalajara International (GDL)

Cheapest

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

📍 ~16 km from Guadalajara (reachable by car)

💸 Flights from ~$250

Airports nearby Guadalajara used as alternative

Del Bajío International (BJX)

Del Bajío International is a major regional hub with extensive domestic and international connections to the US.

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

💸 Flights from ~$309

Business & First Class Flight Deals to Guadalajara

81% AI deal score

$1,147

$813

Save $334

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 for bookings made very close to departure, with flights booked 0-6 days out averaging around $603. Conversely, booking much further in advance, such as 60+ days out, also shows a higher average price of $395 compared to the best window.

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 in the trailing 90 days. Travelers aiming for a budget-friendly trip should target fares at or below the $283 threshold.

Historically, the cheapest months to fly from Chicago to Guadalajara are March, January, and February. March typically sees a median price of $145, while January has a median of $178. February also offers relatively lower prices with a median of $190. These months are considerably cheaper than the annual median price of $439 for this route.

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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: $264 - $579

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

The regular price range for flights from Chicago to Guadalajara is typically between $264 and $579. The current lowest deal is $252 with Aeroenlaces Nacionales for travel from Sep 1-Sep 10.

now $252

Low $264

High $579

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

Aeroenlaces Nacionales

Last-minute flights going from Chicago to Guadalajara

Thu, Aug 13

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$432

$273

One-way

Sun, Aug 23

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$485

$280

One-way

Sun, Aug 23

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$514

$287

One-way

Mon, Aug 24

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$407

$270

One-way

Mon, Aug 24

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$484

$271

One-way

Mon, Aug 24

⌛ Last-Minute

ORD - Guadalajara

Chicago (ORD) - Guadalajara (GDL)

Aeroenlaces Nacionales

$500

$277

One-way

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

4 nights

Dec 3 - Dec 7

$582 → $300

48%

5 nights

Dec 8 - Dec 13

$589 → $307

48%

3 nights

Dec 8 - Dec 11

$588 → $307

48%

4 nights

Dec 8 - Dec 12

$587 → $307

48%

Popular Airports to fly from Chicago to Guadalajara