Can I fly direct from Guadalajara to Chicago?

Historically, approximately 22% of flights from Guadalajara to Chicago have been direct. For routes that include stopovers, travelers typically encounter a median of 2 stopovers. This data reflects trends observed over the trailing 90 days.

How long is the flight from Guadalajara to Chicago?

The typical direct flight from Guadalajara to Chicago has a median duration of 4 hours and 6 minutes. For flights with one stop, the median duration extends to 8 hours and 25 minutes. The approximate distance covered on this route is 2780 kilometers.

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

Based on historical data from the trailing 30 days, deals for flights from Guadalajara to Chicago are classified as frequent. This suggests that price fluctuations are common, and setting a price alert could be beneficial for travelers seeking optimal fares.

Flights From Guadalajara

To Chicago

Cheap Flights from Guadalajara to Chicago

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 2 days ago

451 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Aug 17, 2026.)

Today’s best flight deals from Guadalajara to Chicago

Explore current cheapest deals departing from Guadalajara to Chicago

2026-08-27 – 2026-08-30
GDL - Chicago
82% AI deal score
$383
$248
Round trip
2027-02-17 – 2027-02-25
GDL - Chicago
71% AI deal score
$308
$259
Round trip
2027-02-22 – 2027-02-25
GDL - Chicago
71% AI deal score
$313
$259
Round trip
2026-11-06 – 2026-11-10
GDL - Chicago
79% AI deal score
$351
$263
Round trip
2027-02-24 – 2027-02-25
GDL - Chicago
83% AI deal score
$431
$264
Round trip
2026-11-07 – 2026-11-09
GDL - Chicago
68% AI deal score
$287
$266
Round trip
2026-11-07 – 2026-11-10
GDL - Chicago
68% AI deal score
$287
$267
Round trip
2027-02-16 – 2027-02-25
GDL - Chicago
69% AI deal score
$297
$267
Round trip
2027-02-10 – 2027-02-25
GDL - Chicago
50% AI deal score
$243
$267
Round trip
2026-11-12 – 2026-11-15
GDL - Chicago
68% AI deal score
$287
$268
Round trip

Guadalajara to Chicago: Overview

Insights for flights from Guadalajara to Chicago

Fares for cheap flights from Guadalajara to Chicago typically range from $324–$644, with a median of $480. Right now, prices are near the typical level for this route. New deals for this route appear almost daily, suggesting a dynamic market for travelers.

When is the cheapest time to fly from Guadalajara to Chicago? The data indicates that September is typically the most affordable month, with a median fare of $254. Following closely are December, with a median of $260, and June, at $264. These months offer the lowest median prices for this route.

Most itineraries for flights from Guadalajara to Chicago connect at least once, with only 22% of recent fares being non-stop. For connecting flights, the typical number of stopovers is 2. This means you will likely encounter at least one connection on your journey.

A typical journey from Guadalajara to Chicago takes about 11h 37m, including connections. This medium-haul route covers a distance of 2780 km. Given that most itineraries involve connections, this duration reflects the total travel time rather than just the in-air flight time.

How much is a round trip from Guadalajara to Chicago

Regular price: $312 - $426

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

The regular price range for flights from Guadalajara to Chicago is typically between $312 and $426. The current lowest deal is $248 with Volaris, for travel from Aug 27-Aug 30.

now $248

Low $312

High $426

The cheapest time to fly from Guadalajara to Chicago

Flights from GDL to CHI are cheapest in September, with a median price of $254. The most expensive month to fly is October, with a median price of $589. Generally, prices are lower from February to December.

September

Cheapest

Flights from $254

October

Most Expensive

Flights from $589

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Guadalajara to Chicago

Aeroenlaces Nacionales

Frontier Airlines

Last-minute flights going from Guadalajara to Chicago

Wed, Aug 19

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (ORD)

Volaris

$617

$444

One-way

Thu, Aug 20

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (RFD)

Volaris

$705

$488

One-way

Fri, Aug 21

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (ORD)

Volaris

$607

$428

One-way

Sun, Aug 23

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (RFD)

Volaris

$792

$465

One-way

Sun, Aug 23

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (RFD)

Volaris

$758

$481

One-way

Mon, Aug 24

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (ORD)

Volaris

$570

$400

One-way

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

5 nights

Aug 18 - Aug 23

$849 → $436

49%

6 nights

Aug 18 - Aug 24

$789 → $438

44%

7 nights

Aug 18 - Aug 25

$786 → $438

44%

5 nights

Aug 23 - Aug 28

$772 → $464

40%

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 $480.

📅 Best time to fly

September is historically cheapest

Historically, September is the cheapest month to fly from Guadalajara to Chicago, with a median of $254.

⏱️ Flight duration

Typically 11h 37m

Flights from Guadalajara to Chicago typically take 11 hours 37 minutes, covering 2780 km.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 78% of routes, with a median of 2 stopovers.

🏆 Airline highlight

Volaris has a $248 deal

Volaris offers a recent deal for $248 from August 27-August 30, a below-regular price.

🎯 Booking tip

Deals are frequent

Deals for this route are frequent, appearing often over a 30-day window.

Guadalajara main airports to depart from

Guadalajara International (GDL)

Cheapest

Guadalajara International Airport offers the cheapest flights from Guadalajara to Chicago.

📍 ~20 km from Guadalajara (reachable by car)

💸 Flights from ~$272

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.

📍 ~20 km from Chicago city center (reachable by car)

💸 Flights from ~$272

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and is easily accessible from Chicago.

📍 ~135 km from Chicago (reachable by car or train)

💸 Flights from ~$519

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

Dec 08

Chicago, United States

90% AI deal score

$1,807

$853

Save $954

Aeroméxico

Business Class

From GDL

Elite

Dec 27

Chicago, United States

90% AI deal score

$1,824

$869

Save $955

Aeroméxico

Business Class

From GDL

Elite

Sep 25

Chicago, United States

90% AI deal score

$1,794

$885

Save $909

United Airlines

Business Class

From GDL

Elite

Dec 17

Chicago, United States

89% AI deal score

$1,801

$880

Save $921

Aeroméxico

Business Class

From GDL

Elite

Sep 27

Chicago, United States

89% AI deal score

$1,843

$951

Save $892

United Airlines

Business Class

From GDL

Elite

Dec 17

Chicago, United States

89% AI deal score

$1,190

$645

Save $545

Aeroméxico

Business Class

From GDL

Elite

Dec 29

Chicago, United States

89% AI deal score

$1,178

$645

Save $533

Aeroméxico

Business Class

From GDL

Elite

Dec 19

Chicago, United States

89% AI deal score

$1,190

$645

Save $545

Aeroméxico

Business Class

From GDL

Elite

Dec 29

Chicago, United States

89% AI deal score

$1,183

$647

Save $536

Aeroméxico

Business Class

From GDL

Elite

Dec 20

Chicago, United States

89% AI deal score

$1,186

$648

Save $538

Aeroméxico

Business Class

From GDL

Elite

Dec 22

Chicago, United States

89% AI deal score

$1,187

$648

Save $539

Aeroméxico

Business Class

From GDL

Elite

Dec 25

Chicago, United States

89% AI deal score

$1,187

$648

Save $539

Aeroméxico

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Guadalajara to Chicago is typically 7-13 days before departure. During this period, the average price for a flight has been observed at approximately $311. Booking within 0-6 days of departure sees a slight increase to an average of $346. Conversely, booking 28-59 days out has historically resulted in higher average prices, around $504.

Across the trailing quarter, a good price for a flight from Guadalajara to Chicago is considered to be $324 or less. The median price for this route has historically been $480. Prices can vary, with 75% of fares typically falling below $644 in the trailing 90 days.

Historically, September has been the cheapest month to fly from Guadalajara to Chicago, with a median price of $254. December and June also offer relatively low median prices, at $260 and $264 respectively. The annual median price for this route across the trailing 270 days is $480, indicating that certain months can offer significant savings.

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: $312 - $426

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

The regular price range for flights from Guadalajara to Chicago is typically between $312 and $426. The current lowest deal is $248 with Volaris, for travel from Aug 27-Aug 30.

now $248

Low $312

High $426

The cheapest time to fly from Guadalajara to Chicago

September

Cheapest

Flights from $254

October

Most Expensive

Flights from $589

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Guadalajara to Chicago

Aeroenlaces Nacionales

Frontier Airlines

Last-minute flights going from Guadalajara to Chicago

Wed, Aug 19

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (ORD)

Volaris

$617

$444

One-way

Thu, Aug 20

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (RFD)

Volaris

$705

$488

One-way

Fri, Aug 21

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (ORD)

Volaris

$607

$428

One-way

Sun, Aug 23

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (RFD)

Volaris

$792

$465

One-way

Sun, Aug 23

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (RFD)

Volaris

$758

$481

One-way

Mon, Aug 24

⌛ Last-Minute

GDL - Chicago

Guadalajara (GDL) - Chicago (ORD)

Volaris

$570

$400

One-way

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

5 nights

Aug 18 - Aug 23

$849 → $436

49%

6 nights

Aug 18 - Aug 24

$789 → $438

44%

7 nights

Aug 18 - Aug 25

$786 → $438

44%

5 nights

Aug 23 - Aug 28

$772 → $464

40%

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 $480.

📅 Best time to fly

September is historically cheapest

Historically, September is the cheapest month to fly from Guadalajara to Chicago, with a median of $254.

⏱️ Flight duration

Typically 11h 37m

Flights from Guadalajara to Chicago typically take 11 hours 37 minutes, covering 2780 km.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 78% of routes, with a median of 2 stopovers.

🏆 Airline highlight

Volaris has a $248 deal

Volaris offers a recent deal for $248 from August 27-August 30, a below-regular price.

🎯 Booking tip

Deals are frequent

Deals for this route are frequent, appearing often over a 30-day window.

Guadalajara main airports to depart from

Guadalajara International (GDL)

Cheapest

Guadalajara International Airport offers the cheapest flights from Guadalajara to Chicago.

📍 ~20 km from Guadalajara (reachable by car)

💸 Flights from ~$272

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.

📍 ~20 km from Chicago city center (reachable by car)

💸 Flights from ~$272

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and is easily accessible from Chicago.

Chicago, United States

89% AI deal score

$1,187

$648

Save $539

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

September is historically cheapest

Typically 11h 37m

Connecting flights are dominant

Volaris has a $248 deal

Deals are frequent

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

Dec 08

Dec 27

Sep 25

Dec 17

Sep 27

Dec 17

Dec 29

Dec 19

Dec 29

Dec 20

Dec 22

Dec 25

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

September is historically cheapest

Typically 11h 37m

Connecting flights are dominant

Volaris has a $248 deal

Deals are frequent

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

Dec 08

Dec 27

Sep 25

Dec 17

Sep 27

Dec 17

Dec 29

Dec 19

Dec 29

Dec 20

Dec 22

Dec 25

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?