Cheap Flights from Chicago to Monterey
Cheap Flights from Chicago to Monterey
Looking for cheap flights from Chicago to Monterey? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to Monterey vary by season, cabin, and date, but available award flights can start around 12,500–15,000 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to Monterey for specific travel dates.
2026-12-04
ORD - MRY
Economy | 1 Stop
From 12,500 Pts + $5.6
2026-12-05
ORD - MRY
Economy | 1 Stop | 9+ left
From 12,500 Pts + $5.6
2026-12-05
ORD - MRY
Economy | 1 Stop
From 12,500 Pts + $5.6
2026-12-06
ORD - MRY
Economy | 1 Stop
From 12,500 Pts + $5.6
2026-12-04
ORD - MRY
Economy | 1 Stop | 9+ left
From 15,000 Pts + $5.6
2026-12-05
ORD - MRY
Economy | 1 Stop
From 15,000 Pts + $5.6
Chicago to Monterey flight facts
Distance
1,837 mi
2,956 km in a straight line
Estimated flight time
about 4h 15m
In the air, for the straight-line distance
Time difference
−2h
Monterey is 2 hours behind Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Monterey
MRY · Monterey Peninsula
Nearby airport alternatives
Flights Chicago - San Jose · San Jose is 54 mi from Monterey
Flights Chicago - San Francisco · San Francisco is 77 mi from Monterey
Flights Chicago - Oakland · Oakland is 81 mi from Monterey
Flights South Bend - Monterey · South Bend is 86 mi from Chicago
Flights Chicago - San Luis Obispo · San Luis Obispo is 115 mi from Monterey
Flights Chicago - Fresno · Fresno is 118 mi from Monterey
Premium cabin flights from Chicago to Monterey
Premium cabin
2026-12-04
ORD - MRY
First | 1 Stop | 3 left
From 30,000 Pts + $11.2
Premium cabin
2026-12-06
ORD - MRY
First | 1 Stop | 2 left
From 35,000 Pts + $25.6
Premium cabin
2026-12-05
ORD - MRY
First | 1 Stop
From 43,600 Pts + $5.6
Selected hotels for your next stay
No hotels available at the moment. Check back soon!
Frequently Asked Questions
The cheapest route from Chicago to Monterey depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to Monterey.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Monterey.
Chicago and Monterey are about 1,837 miles (2,956 km) apart in a straight line.
Flying the 1,837-mile straight-line distance takes about 4h 15m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Monterey is 2 hours behind Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Monterey: Monterey Peninsula (MRY).
Travelers searching this route also look at other popular routes into Monterey, plus the return trip when we track it. Fares and award space change daily.
Our mission is to provide
the simplest and best
points travel planning
experience. Yeah!
Our mission is to provide the simplest and best
points travel planning experience. Yeah!
