How to get from Chicago to Guadalajara: connecting flights, about 8h 12m total

Flights from Chicago to Guadalajara

Pick a departure date to see flights and seller prices

We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.

Prices by day: Chicago to Guadalajara

Lowest one-way price in dollars from recent searches, cheap days in green. Press a day to see flights and exact prices.

Best fares from Chicago to Guadalajara

Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date

Cheapest one-way $119 11 November 2026, nonstop Cheapest nonstop $119 11 November 2026, F9 Cheapest in the next 7 days $119 Today Cheapest weekend departure $386 Sat, 19 December 2026

Cheapest day of the week Wednesday $210 on average over the next 120 days

Cheapest month November 2026 tickets from $119

Where to connect

Options with one connection, fastest first

fastest, via Monterrey: 8h 12m
two tickets, via Mexico City: $174
connection options: 5
straight-line distance: 1,729 mi (2,782 km)

fastest

Via Monterrey

Mexico

8h 12m

with the connection

Chicago to Monterrey flight 3h 40m

Connection of about 3h

Monterrey to Guadalajara flight 1h 32m

Via Dallas

8h 23m

with the connection

Chicago to Dallas flight 2h 40m

Connection of about 3h Arrival: Dallas Love Field, Dallas/Fort Worth International. Departure to Guadalajara: Dallas/Fort Worth International.

Dallas to Guadalajara flight 2h 43m

two ticketsfrom $311

Via Puerto Vallarta

Mexico

8h 43m

with the connection

Chicago to Puerto Vallarta flight 4h 45m

Connection of about 3h

Puerto Vallarta to Guadalajara flight 58m

Via Mexico City

Mexico

8h 57m

with the connection

Chicago to Mexico City flight 4h 26m

Connection of about 3h

Mexico City to Guadalajara flight 1h 31m

two ticketsfrom $174

Via Cancun

Mexico

9h 46m

with the connection

Chicago to Cancun flight 3h 51m

Connection of about 3h

Cancun to Guadalajara flight 2h 55m

One ticket or two

How the options are calculated and what to keep in mind at the connection

Flight times come from the nonstop schedule (estimated from the distance where there is no schedule), with 3h allowed for the connection. The price of an option is the sum of the lowest known fares for each leg; their dates may not match, so treat it as a guide. The search shows tickets for your dates, including connections on a single ticket.

Nearest nonstop flights

The closest you can get without a connection

From Chicago to cities closest to Guadalajara

Chicago to Leon/Guanajuato Leon/Guanajuato: 112 mi (180 km) from Guadalajara, flight 4h 11m from $167 Chicago to Puerto Vallarta Puerto Vallarta: 121 mi (195 km) from Guadalajara, flight 4h 45m Chicago to Morelia Morelia: 155 mi (249 km) from Guadalajara, flight 4h 9m from $115 Chicago to Mexico City Mexico City: 287 mi (462 km) from Guadalajara, flight 4h 26m from $114 Chicago to Monterrey Monterrey: 397 mi (639 km) from Guadalajara, flight 3h 40m Chicago to San Jose Del Cabo San Jose Del Cabo: 443 mi (713 km) from Guadalajara, flight 4h 52m from $263

To Guadalajara from cities closest to Chicago

Detroit to Guadalajara Detroit: 237 mi (381 km) from Chicago, flight 5h 20m Toronto to Guadalajara Toronto: 436 mi (701 km) from Chicago, flight 5h 25m from $198 New York to Guadalajara New York: 711 mi (1,144 km) from Chicago, flight 6h 10m from $178 Dallas to Guadalajara Dallas: 805 mi (1,295 km) from Chicago, flight 2h 43m from $193 San Antonio to Guadalajara San Antonio: 1,053 mi (1,694 km) from Chicago, flight 2h 2m from $302 Miami to Guadalajara Miami: 1,191 mi (1,917 km) from Chicago, flight 4h 7m from $120

Frequently asked questions

Is there a nonstop flight from Chicago to Guadalajara?

There are no nonstop flights in the schedule. You will need a connection, the fastest is via Monterrey.

What is the fastest way to fly from Chicago to Guadalajara?

Via Monterrey: 3h 40m to the connection, 1h 32m after it, about 8h 12m in total with 3h for the connection.

How much does a flight from Chicago to Guadalajara with a connection cost?

Two nonstop tickets via Mexico City from $174. This is the sum of the lowest known prices for each leg, and their dates may not match.

Which cities can you connect in between Chicago and Guadalajara?

Monterrey (8h 12m total), Dallas (8h 23m total), Puerto Vallarta (8h 43m total), Mexico City (8h 57m total) and Cancun (9h 46m total).

How far is Guadalajara from Chicago?

1,729 mi (2,782 km) in a straight line between the cities.

How much time should I allow for the connection?

The options allow 3h. On a single ticket the carrier is responsible for the connection; on separate tickets you set the margin yourself, allowing time to collect and re-check your bags.