Cheap flights from Chicago to Monterey

One-way fares from $204 · CHI → MRY · prices found by travellers in the last 48 hours

Compare all dates Monterey → Chicago
Cheapest fare
$204

Alaska Airlines · Tue, Dec 15

Cheapest month
December

from $204

Direct flights
Not recently

Usually 1+ stop

Quickest trip
6h 13m

2,990 km

Get a price alert

We'll email you when Chicago → Monterey drops to your price. It's free, and you can stop any time.

Today's cheapest fare is $204. We'll send one email to confirm. See our privacy policy.

Cheapest month to fly from Chicago to Monterey

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. December 2026 Cheapest $204

Cheapest dates in December 2026

The lowest fares we've seen for each day, cheapest first.

Alaska Airlines
Depart07:27 Tue, Dec 15ORD → MRY 6h 13m · 1 stop
$204one way, per person
View deal
See every date in December 2026 →

Plan the rest of your trip to Monterey

Where to stay, what to do and getting around, from our travel partners.

Where to stay

Hotels in MontereyCompare places to stay on Booking.com Find hotels →

Things to do

Things to do in MontereyTours, attractions and day trips on Klook Explore →

Getting around

Airport transfer in MontereyPre-book a driver to meet you at arrivals, with Kiwitaxi Book a transfer → Car hire in MontereyCompare rental cars from major brands on EconomyBookings Compare cars →

About flights from Chicago to Monterey

Chicago (CHI) and Monterey (MRY) are about 2,990 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 6h 13m. Over the next few months, one-way fares start from $204, and December 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Chicago to Monterey?

The cheapest one-way fare we've seen recently is $204 with Alaska Airlines, departing Tuesday, December 15, 2026.

What is the cheapest month to fly from Chicago to Monterey?

December 2026 currently has the lowest fares, from $204 one way.

Are there direct flights from Chicago to Monterey?

We haven't seen direct fares recently, so most journeys include at least one stop.

How long is the flight from Chicago to Monterey?

The quickest journey we've seen takes about 6h 13m. Chicago and Monterey are around 2,990 km apart.

Which airlines fly from Chicago to Monterey?

Recent fares on this route were with Alaska Airlines.

More cheap flights from Chicago

Compare flights to Monterey from other cities →