Featured airlines
- Plan, book, fly with confidence
- Be in the knowGet alerts if flight prices drop or rise*
- Book smarterSave up to 30% on select hotels after you book a flight*
Cheap Flights from Monterey to Chicago (MRY-ORD)
Prices were available within the past 7 days and start at $156 for one-way flights and $340 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Origin airport | Monterey Peninsula |
Destination airport | O'Hare Intl. |
Airlines serving | Alaska Airlines, American Airlines, Hawaiian Airlines, United |
Roundtrip price | $339 |
Distance | 1840 mi |
Monterey to Chicago Flights
The cheapest times to fly from Monterey to Chicago
On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Monterey to Chicago are during the month of May. You can find some of the cheapest flights from Monterey to Chicago with Expedia's search tool and vast selection of airlines.
The best time to book a flight from Monterey to Chicago
Sunday is one of the best days to book for cheap flights from Monterey to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.
How to find cheap round-trip tickets from Monterey to Chicago
Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Monterey to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $156 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.
Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Monterey to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.
You could also save big by booking one of Expedia's vacation packages. Bundling together your Monterey to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.
*Terms apply.
Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.
Frequently asked questions
Explore a world of travel with Expedia
Flights
- Flights from Stockton Municipal
- Flights from Watsonville Municipal
- Flights from Merced Municipal
- Flights from Norman Y. Mineta San Jose Intl.
- Flights from Mesa Del Rey
- Flights from San Francisco Intl.
- Flights from Oakland Intl.
- Flights from Modesto City - County
- Flights from San Carlos
- Flights from Salinas Municipal
- Hawaiian Airlines
- Austrian Airlines
- United
- Air New Zealand
- Lufthansa
- Alaska Airlines
- Air Canada
- avianca
- Qatar Airways
- Copa
- American Airlines
- Japan Airlines
- Flights from Chicago (ORD) to Phoenix (PHX)
- Flights from Monterey (MRY) to Phoenix (PHX)
- Flights from Monterey (MRY) to Greenville (GSP)
- Flights from Los Angeles (LAX) to Tokyo (NRT)
- Flights from San Francisco (SFO) to Tokyo (NRT)
- Flights from Los Angeles (LAX) to New York (NYC)
- Flights from Monterey (MRY) to Portland (PDX)
- Flights from Monterey (MRY) to Palm Springs (PSP)
- Flights from Los Angeles (LAX) to San Francisco (SFO)
- Flights from Chicago (ORD) to Los Angeles (LAX)
- Flights from Monterey (MRY) to Los Angeles (LAX)
- Flights from Atlanta (ATL) to Los Angeles (LAX)
- Flights from New York (NYC) to Los Angeles (LAX)
- Flights from San Francisco (SFO) to Los Angeles (LAX)
- Flights from Dallas (DFW) to Los Angeles (LAX)
- Flights from Seattle (SEA) to Los Angeles (LAX)
- Flights from Las Vegas (LAS) to Los Angeles (LAX)
- Flights from Monterey (MRY) to Denver (DEN)
- Flights from Chicago (ORD) to Orlando (MCO)
- Flights from Monterey (MRY) to Charlotte (CLT)
- Flights from Chicago (ORD) to Las Vegas (LAS)
- Flights from Los Angeles (LAX) to Las Vegas (LAS)
- Flights from San Francisco (SFO) to Las Vegas (LAS)
- Flights from Monterey (MRY) to Honolulu (HNL)
- Flights from Los Angeles (LAX) to Honolulu (HNL)
- Flights from Los Angeles (LAX) to Miami (MIA)
- Flights from Chicago (ORD) to Miami (MIA)
- Flights from Monterey (MRY) to Guadalajara (GDL)
- Flights from Monterey (MRY) to Guatemala City (GUA)
- Flights from Los Angeles (LAX) to Paris (CDG)
- Flights from San Francisco (SFO) to New York (JFK)
- Flights from Los Angeles (LAX) to Manila (MNL)
- Flights from Los Angeles (LAX) to Cancun (CUN)
- Flights from Los Angeles (LAX) to Dallas (DFW)
- Flights from Monterey (MRY) to San Diego (SAN)
- Flights from Los Angeles (LAX) to Seoul (ICN)
- Flights from Los Angeles (LAX) to Seattle (SEA)
- Flights from Monterey (MRY) to Seattle (SEA)
- Flights from Los Angeles (LAX) to London (LHR)
- Flights from Los Angeles (LAX) to Bangkok (BKK)
- Flights from Phoenix (PHX) to Chicago (ORD)
- Flights from Fort Lauderdale (FLL) to Chicago (ORD)
- Flights from Miami (MIA) to Chicago (ORD)
- Flights from Dallas (DFW) to Chicago (ORD)
- Flights from Denver (DEN) to Chicago (ORD)
- Flights from Boston (BOS) to Chicago (ORD)
- Flights from Tampa (TPA) to Chicago (ORD)
- Flights from Los Angeles (LAX) to Chicago (ORD)
- Flights from Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
- Flights from Dallas (DAL) to Chicago (ORD)
- Flights from New York (LGA) to Chicago (ORD)
- Flights from Charlotte (CLT) to Chicago (ORD)
- Flights from New York (JFK) to Chicago (ORD)
- United Monterey (MRY) to Los Angeles (LAX) flights
- United Monterey (MRY) to Ontario (ONT) flights
- Alaska Airlines Monterey (MRY) to San Diego (SAN) flights
- Alaska Airlines Monterey (MRY) to Seattle (SEA) flights
- Spirit Airlines New York (LGA) to Chicago (ORD) flights
- JetBlue Airways Boston (BOS) to Chicago (ORD) flights
- JetBlue Airways New York (JFK) to Chicago (ORD) flights
- Spirit Airlines Charlotte (CLT) to Chicago (ORD) flights
- Alaska Airlines Phoenix (PHX) to Chicago (ORD) flights
- Spirit Airlines Tampa (TPA) to Chicago (ORD) flights
- Frontier Airlines Denver (DEN) to Chicago (ORD) flights
- Alaska Airlines Los Angeles (LAX) to Chicago (ORD) flights
- American Airlines Miami (MIA) to Chicago (ORD) flights
- JetBlue Airways Fort Lauderdale (FLL) to Chicago (ORD) flights
- Flights to New York
- Flights to Key West
- Flights to Miami
- Flights to Pigeon Forge
- Flights to Boston
- Flights to Chicago
- Flights to Fort Lauderdale
- Flights to New Orleans
- Flights to San Antonio
- Flights to Las Vegas
- Flights to Houston
- Flights to Los Angeles
- Flights to Honolulu
- Flights to Gatlinburg
- Flights to San Diego
- Flights to Atlanta
- Flights to Nashville
- Flights to San Francisco
- Flights to Orlando
- Flights to Washington