Can I fly direct from Guadalajara to Chicago?

Direct flights from Guadalajara to Chicago are available, though they represent a smaller portion of the total routes. Historically, approximately 10.3% of flights on this route have been direct. For flights with stopovers, travelers typically encounter 2 stopovers when connecting between these two cities.

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

Given that flights from Guadalajara to Chicago are classified as a regular deal route, setting a price alert is a good strategy. This indicates that price fluctuations and deals occur with some consistency. Monitoring prices can help travelers secure a more favorable fare for their journey.

Flights From Guadalajara

To Chicago

Cheap Flights from Guadalajara to Chicago

Q: How long is the flight from Guadalajara to Chicago?

The direct flight from Guadalajara to Chicago typically takes about 4 hours and 6 minutes. This route covers an approximate distance of 2780 kilometers. Flights with one stopover, on average, have a significantly longer duration, typically taking around 13 hours and 39 minutes.

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

Deals from

Guadalajara

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

Prices updated 4 days ago

476 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 12, 2026.)

Today’s best flight deals from Guadalajara to Chicago

Explore current cheapest deals departing from Guadalajara to Chicago

2027-01-31 – 2027-02-27
GDL - Chicago
79% AI deal score
$314
$241
Round trip
2027-01-31 – 2027-02-17
GDL - Chicago
78% AI deal score
$316
$249
Round trip
2027-01-31 – 2027-02-10
GDL - Chicago
79% AI deal score
$327
$249
Round trip
2027-02-05 – 2027-02-27
GDL - Chicago
72% AI deal score
$288
$249
Round trip
2027-01-31 – 2027-02-20
GDL - Chicago
78% AI deal score
$314
$249
Round trip
2026-10-21 – 2026-11-09
GDL - Chicago
71% AI deal score
$294
$253
Round trip
2027-02-10 – 2027-02-27
GDL - Chicago
72% AI deal score
$291
$254
Round trip
2026-10-21 – 2026-11-08
GDL - Chicago
71% AI deal score
$295
$255
Round trip
2026-10-21 – 2026-11-15
GDL - Chicago
71% AI deal score
$292
$255
Round trip
2027-02-08 – 2027-02-27
GDL - Chicago
71% AI deal score
$290
$256
Round trip

Guadalajara to Chicago: Overview

Insights for flights from Guadalajara to Chicago

Right now, fares for cheap flights from Guadalajara to Chicago are near the typical level. Over the past 90 days, 13% of observed fares were classified as a good price. Prices typically range from $467–$877, with a median of $631.

When is the cheapest time to fly from Guadalajara to Chicago? The data indicates that October is typically the most affordable month, with a median fare of $360. February also offers competitive pricing, with a median of $362. Travelers might also find more favorable prices in August, where the median fare is $539.

A typical journey from Guadalajara to Chicago is a medium-haul flight, covering a distance of 2780 km. Most itineraries connect at least once, with only 10.3% of recent fares being non-stop. For connecting flights, the median number of stopovers is 2.

How long is the flight from Guadalajara to Chicago? A typical journey, including connections, takes about 23h 37m. For the limited direct flights from Guadalajara to Chicago, the median flight time is 4h 6m. Given that most itineraries involve connections, the overall travel time tends to be significantly longer.

How much is a round trip from Guadalajara to Chicago

Regular price: $282 - $543

Prices are currently below the regular range.

The regular price range for flights from Guadalajara to Chicago is $282-$543. The current lowest deal is $242 with Volaris for travel from Jan 31-Feb 27.

now $242

Low $282

High $543

The cheapest time to fly from Guadalajara to Chicago

The cheapest month to fly from GDL to CHI is October, with a median price of $360. The most expensive month is December, with a median price of $856. Prices are generally lower from February to November.

October

Cheapest

Flights from $360

December

Most Expensive

Flights from $856

Feb

Mar

Apr

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Guadalajara to Chicago

Volaris

Last-minute flights going from Guadalajara to Chicago

Sat, Oct 10

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (MDW)

Aeroméxico

$755

$530

One-way

Sun, Oct 11

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (ORD)

Volaris

$605

$431

One-way

Mon, Oct 12

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (ORD)

Aeroenlaces Nacionales

$612

$390

One-way

Mon, Oct 12

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (ORD)

Aeroenlaces Nacionales

$605

$418

One-way

Mon, Oct 12

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (ORD)

Aeroenlaces Nacionales

$551

$427

One-way

Tue, Oct 13

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (ORD)

Aeroenlaces Nacionales

$603

$360

One-way

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

3 nights

Oct 9 - Oct 12

$605 → $315

48%

1 night

Oct 9 - Oct 10

$613 → $333

46%

1 night

Oct 8 - Oct 9

$613 → $348

43%

2 nights

Oct 8 - Oct 10

$612 → $355

42%

Popular Airports to fly from Guadalajara to Chicago

Guadalajara - Chicago route insights

💸 Price insights

Recent fares near the typical level

Recent fares for Guadalajara to Chicago are near the typical level of $631.

📅 Best time to fly

October offers the lowest median price

Historically, October is the cheapest month to fly, with a median price of $360.

⏱️ Flight duration

Direct flights average 4h 6m

The typical direct flight from Guadalajara to Chicago takes 4h 6m.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights are dominant, with a median of 2 stopovers for this route.

🏆 Airline highlight

Volaris offers direct flights

Volaris provides direct flights from Guadalajara to Chicago.

🎯 Booking tip

Deals appear regularly

Deals for flights from Guadalajara to Chicago appear regularly, typically within 30 days.

Guadalajara main airports to depart from

Guadalajara International (GDL)

Cheapest

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

📍 ~16 km from Guadalajara (reachable by car)

💸 Flights from ~$235

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering extensive connections for your trip to Chicago.

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

💸 Flights from ~$246

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 train or car across state lines).

💸 Flights from ~$426

Business & First Class Flight Deals to Chicago

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

Elite

Best Elite deals to Chicago

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

From GDL

Elite

Mar 04

Chicago, United States

90% AI deal score

$1,446

$761

Save $685

United Airlines

Business Class

From GDL

Elite

Mar 22

Chicago, United States

90% AI deal score

$1,509

$796

Save $713

United Airlines

Business Class

From GDL

Elite

Dec 13

Chicago, United States

90% AI deal score

$1,644

$821

Save $823

Aeroméxico

Business Class

From GDL

Elite

Dec 15

Chicago, United States

90% AI deal score

$1,651

$821

Save $830

Aeroméxico

Business Class

From GDL

Elite

Dec 12

Chicago, United States

90% AI deal score

$1,647

$821

Save $826

Aeroméxico

Business Class

From GDL

Elite

Dec 14

Chicago, United States

90% AI deal score

$1,651

$821

Save $830

Aeroméxico

Business Class

From GDL

Elite

Dec 14

Chicago, United States

90% AI deal score

$1,139

$614

Save $525

Aeroméxico

Business Class

From GDL

Elite

Dec 15

Chicago, United States

90% AI deal score

$1,139

$614

Save $525

Aeroméxico

Business Class

From GDL

Elite

Dec 12

Chicago, United States

90% AI deal score

$1,135

$614

Save $521

Aeroméxico

Business Class

From GDL

Elite

Dec 13

Chicago, United States

90% AI deal score

$1,130

$614

Save $516

Aeroméxico

Business Class

From GDL

Elite

Dec 14

Chicago, United States

90% AI deal score

$1,144

$614

Save $530

Aeroméxico

Business Class

From GDL

Elite

Dec 15

Chicago, United States

90% AI deal score

$1,139

$614

Save $525

Aeroméxico

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Guadalajara to Chicago is typically 14-27 days before departure. During this period, the average price observed was $340. Booking within 0-6 days of departure generally sees prices rise significantly, with an average of $796. Conversely, booking 60+ days out also tends to be more expensive, averaging $739.

Across the trailing quarter, a good price for a flight from Guadalajara to Chicago is considered to be $467 or less. The median price for this route historically stands at $631. Prices can range higher, with 75% of fares observed being $877 or less in the trailing 90 days.

Historically, October and February have been the cheapest months to fly from Guadalajara to Chicago, with median prices of $360 and $362 respectively. The most expensive month observed in the trailing 270 days was August, with a median price of $539. The overall annual median price for this route is $631.

Related routes

More routes from Guadalajara

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Guadalajara to Chicago: Overview

Insights for flights from Guadalajara to Chicago

How much is a round trip from Guadalajara to Chicago

Regular price: $282 - $543

Prices are currently below the regular range.

The regular price range for flights from Guadalajara to Chicago is $282-$543. The current lowest deal is $242 with Volaris for travel from Jan 31-Feb 27.

now $242

Low $282

High $543

The cheapest time to fly from Guadalajara to Chicago

October

Cheapest

Flights from $360

December

Most Expensive

Flights from $856

Feb

Mar

Apr

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Guadalajara to Chicago

Volaris

Last-minute flights going from Guadalajara to Chicago

Sat, Oct 10

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (MDW)

Aeroméxico

$755

$530

One-way

Sun, Oct 11

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (ORD)

Volaris

$605

$431

One-way

Mon, Oct 12

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (ORD)

Aeroenlaces Nacionales

$612

$390

One-way

Mon, Oct 12

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (ORD)

Aeroenlaces Nacionales

$605

$418

One-way

Mon, Oct 12

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (ORD)

Aeroenlaces Nacionales

$551

$427

One-way

Tue, Oct 13

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (ORD)

Aeroenlaces Nacionales

$603

$360

One-way

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

3 nights

Oct 9 - Oct 12

$605 → $315

48%

1 night

Oct 9 - Oct 10

$613 → $333

46%

1 night

Oct 8 - Oct 9

$613 → $348

43%

2 nights

Oct 8 - Oct 10

$612 → $355

42%

Popular Airports to fly from Guadalajara to Chicago

Guadalajara - Chicago route insights

💸 Price insights

Recent fares near the typical level

Recent fares for Guadalajara to Chicago are near the typical level of $631.

📅 Best time to fly

October offers the lowest median price

Historically, October is the cheapest month to fly, with a median price of $360.

⏱️ Flight duration

Direct flights average 4h 6m

The typical direct flight from Guadalajara to Chicago takes 4h 6m.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights are dominant, with a median of 2 stopovers for this route.

🏆 Airline highlight

Volaris offers direct flights

Volaris provides direct flights from Guadalajara to Chicago.

🎯 Booking tip

Deals appear regularly

Deals for flights from Guadalajara to Chicago appear regularly, typically within 30 days.

Guadalajara main airports to depart from

Guadalajara International (GDL)

Cheapest

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

📍 ~16 km from Guadalajara (reachable by car)

💸 Flights from ~$235

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering extensive connections for your trip to Chicago.

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

💸 Flights from ~$246

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.

Chicago, United States

90% AI deal score

$1,139

$614

Save $525

Aeroméxico

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Guadalajara to Chicago

Today’s best flight deals from Guadalajara to Chicago

Guadalajara to Chicago: Overview

Insights for flights from Guadalajara to Chicago

How much is a round trip from Guadalajara to Chicago

The cheapest time to fly from Guadalajara to Chicago

Direct flights from Guadalajara to Chicago

Last-minute flights going from Guadalajara to Chicago

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

Popular Airports to fly from Guadalajara to Chicago

Guadalajara - Chicago route insights

Recent fares near the typical level

October offers the lowest median price

Direct flights average 4h 6m

Connecting flights are dominant

Volaris offers direct flights

Deals appear regularly

Guadalajara 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

Mar 04

Mar 22

Dec 13

Dec 15

Dec 12

Dec 14

Dec 14

Dec 15

Dec 12

Dec 13

Dec 14

Dec 15

Frequently Asked Questions About Flights to Chicago

When is the best time to book flights from Guadalajara to Chicago?

What's a cheap fare from Guadalajara to Chicago?

What's the cheapest month to fly from Guadalajara to Chicago?

Can I fly direct from Guadalajara to Chicago?

How long is the flight from Guadalajara to Chicago?

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

Related routes

More routes from Guadalajara

Flights to Chicago from other cities

Guadalajara to Chicago: Overview

Insights for flights from Guadalajara to Chicago

How much is a round trip from Guadalajara to Chicago

The cheapest time to fly from Guadalajara to Chicago

Direct flights from Guadalajara to Chicago

Last-minute flights going from Guadalajara to Chicago

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

Popular Airports to fly from Guadalajara to Chicago

Guadalajara - Chicago route insights

Recent fares near the typical level

October offers the lowest median price

Direct flights average 4h 6m

Connecting flights are dominant

Volaris offers direct flights

Deals appear regularly

Guadalajara 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

Mar 04

Mar 22

Dec 13

Dec 15

Dec 12

Dec 14

Dec 14

Dec 15

Dec 12

Dec 13

Dec 14

Dec 15

Frequently Asked Questions About Flights to Chicago

When is the best time to book flights from Guadalajara to Chicago?

What's a cheap fare from Guadalajara to Chicago?

What's the cheapest month to fly from Guadalajara to Chicago?