The cheapest order to fly Mexico City, Guadalajara and Monterrey from Chicago
There are 6 ways to fly these cities, and 2 of them can be priced from fares we have seen. They do not cost the same. The cheapest works out at about $407 a person and the most expensive at $483, a difference of $76 for visiting exactly the same places.
Fly them in this order
Chicago → Mexico City → Monterrey → Guadalajara → Chicago
About $407 per person in flights, based on fares recently seen on these routes, and the cheapest of the 2 ways round we could price.
The 2 we can price
- Chicago → Mexico City → Monterrey → Guadalajara → Chicago$407cheapest order
- Chicago → Guadalajara → Monterrey → Mexico City → Chicago$483$76 more per person
Why Mexico City first
- Chicago to Mexico City$148
- Mexico City to Monterrey$26
- Monterrey to Guadalajara$63
- Guadalajara to Chicago$170
- Out of Chicago, Mexico City is the cheapest first stop at about $148. Guadalajara would be $223.
- Going home, the cheapest flight leaves from Mexico City at about $148, but the cheapest order ends in Guadalajara at $170 because the rest of the route is cheaper that way.
- Mexico City to Guadalajara is about $32, but the other way round is $69. Same two cities, $37 apart on direction alone.
- The dearest order pays $223 for Chicago to Guadalajara, a flight the cheapest order never takes.
- Guadalajara to Chicago is 42% of what the cheapest order spends on flights, so it is the leg to watch.
Between the cities
- 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.
- Monterrey to Guadalajara: about 640 km (400 miles) as the crow flies. Also by ground: ETN / Omnibus de Mexico (overnight), about 11h 30m, usually $60 to $110.
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, 10 of 12 legs priced from real observations, put together on November 12, 2026, from fares departing November 12, 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.
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 16, 2027 to January 30, 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 datesSigned out, 3 trips 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, your first trip also searches Google Flights live, and you can change your trips afterwards.