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The cheapest order to fly Mexico City, Guadalajara and Monterrey from Chicago

There are 6 ways to fly these cities, and 4 of them can be priced from fares we have seen. They do not cost the same. The cheapest works out at about $432 a person and the most expensive at $498, a difference of $66 for visiting exactly the same places.

Fly them in this order

Chicago → Guadalajara → Mexico City → Monterrey → Chicago

About $432 per person in flights, based on fares recently seen on these routes, and the cheapest of the 4 ways round we could price.

The 4 we can price

  1. Chicago → Guadalajara → Mexico City → Monterrey → Chicago$432
    cheapest order
  2. Chicago → Mexico City → Monterrey → Guadalajara → Chicago$461
    $29 more per person
  3. Chicago → Mexico City → Guadalajara → Monterrey → Chicago$485
    $53 more per person
  4. Chicago → Guadalajara → Monterrey → Mexico City → Chicago$498
    $66 more per person

The cheapest order, leg by leg

  1. Chicago to Guadalajara$182
  2. Guadalajara to Mexico City$50
  3. Mexico City to Monterrey$35
  4. Monterrey to Chicago$165
  • Monterrey to Guadalajara is about $55, but the other way round is $89. Same two cities, $34 apart on direction alone.
  • Chicago to Guadalajara is 42% of what the cheapest order spends on flights, so it is the leg to watch.

Between the cities

  • Guadalajara to Mexico City: about 460 km (290 miles) as the crow flies. Also by ground: ETN / Primera Plus, about 7h, usually $45 to $75.
  • Mexico City to Monterrey: about 710 km (440 miles) as the crow flies. Also by ground: ETN / Futura, about 11h 30m, usually $65 to $125.

Entry rules on a US passport

  • US passport: no visa for Mexico; keep the FMM/arrival record if issued. Official source

Rules change; check the official source for your passport and dates before you book.

What these numbers are

Cached one-way fares, 11 of 12 legs priced from real observations, put together on October 29, 2026, from fares departing October 31, 2026 onwards. Right for comparing one order with another, not a quote for your dates.

A plan prices your own dates and weighs hours as well as fares, so it can pick a different order from this page.

Other trips priced this way

From Chicago

Trips through the same cities

Put dates on it

Same cities on real dates, plus what one search cannot show: layovers long enough to count as a free city, two tickets that beat one, and cheaper days either side. No account and no card.

One press starts it on January 2, 2027 to January 16, 2027, 14 days, for 2 travelers. Our dates, not yours, and about two minutes.

Plan Mexico City, Guadalajara and Monterrey from Chicago nowOpen the form instead and pick your own dates

Signed out, 3 plans a day per address, priced from cached fares and the free sources, so some legs may be estimates and the plan says which. Signed in, legs are checked live, with 2 free trips you can change afterwards.