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KAYAK's insights & trends for Chicago to California flights

Get data-powered insights and trends into flights from Chicago to California to help you find the cheapest flights, the best time to fly and much more.

How much is a return flight from Chicago to California?

Flight prices are below average for this route right now.

Flights to California from Chicago usually cost between £164 and £280 in November.
The lowest price found in the past 5 days was £149 on Southwest (9 Nov–15 Nov).

What is the cheapest Chicago to California flight route?

The cheapest ticket to California from Chicago found in the last 5 days was to Oakland, at £194 return. The most popular route is from Chicago O'Hare Intl Airport (ORD) to San Francisco (SFO), and the cheapest return airline ticket found on this route in the last 5 days was £463.

What is the cheapest time of day to fly to California?

The cheapest time of day to fly to California is generally at night, when retur flights cost £217 on average. The most expensive time of day to fly to California is generally in the morning, which is peak travel time and where the average cost of a ticket is £355.

Can I save money by flying with a stopover from Chicago to California?

Yes, flying with a stopover may cost you more time, but you can also save money on the route, with a 1 stop stopover the cheapest option at £299 on average.

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

The cheapest month for flights from Chicago to California is April, when tickets cost £261 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of return tickets is £323 and £304 respectively.

What’s the cheapest day of the week to fly from Chicago to California?

For Chicago to California, Thursday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from California back to Chicago, the best deals are generally found on Monday, with Friday being the most expensive.

How far in advance should I book a flight from Chicago to California?

To get a below-average price on a flight from Chicago to California, you should book around 4 weeks before departure, which saves you about 39% compared to booking last-minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know - Cheap tickets from Chicago to California

Low season

January
Best time to beat the crowds (16% less expensive on average)
Most popular time to fly (3% more expensive on average)

Flights from Chicago to California: the best tips from KAYAK users

Insights shared by verified travellers who flew the route from Chicago to California 
TammiFlew with American Airlines-Sept 2026
In LA - only way to get an uber is to take a bus to an offsite area - can’t get directly at airport.
MarkFlew with American Airlines-Jun 2026
Get there early, only one TSA line open and thew queue was very long.
MikeFlew with American Airlines-Sept 2024
Arrive early, grab a bottle of soda before getting on the plane and open it in the terminal. If you wait until flying the pressure will decarbonize the drink.

FAQs - booking California flights

  • Is ORD accessible to all?

    You can count on having a smooth experience at ORD if you’re disabled, as this airport is accessible to all. To cater to passengers with mobility impairment, it features drop-off areas equipped with curb ranks and mandates each airline that serves flights to California to offer wheelchair assistance. It has also invested in restrooms throughout the airport with wheelchair-accessible facilities. The said restrooms are three in Terminal 1, two in Terminal two, over ten in Terminal 3, and two in Terminal 5.

  • How can I travel to ORD from Downtown Chicago?

    In case you’re set to fly from Chicago’s ORD to California, you can travel to the airport from Downtown Chicago via a Blue Line train, a Metra North Central Service train line, a CTA bus, or a taxi. Boarding a Blue Line train, a Metra North Central service train, or a CTA bus is advisable if you’re on a budget. On the other hand, boarding a taxi is advisable if you value convenience. This is because, unlike its comparisons, a taxi will pick you up at your preferred destination and transport you directly to the airport.

  • Can I breastfeed my baby before my flight to California?

    Regardless of the Chicago airport you’re set to fly out of, you can comfortably breastfeed your baby while waiting for your flight since both transit stations offer nursing rooms equipped with comfortable seats, deep sinks, changing tables, and power outlets. At MDW, the available nursing room is in Concourse C, next to the yoga room. In contrast, at ORD, the rooms are available near gates B4, B10, and C 20 in Terminal 1, between gates E5 and F9 in Terminal 2, the Rotunda and gate L6 in Terminal 3, gate M20 in Terminal 5, and on Level 1 of the Multi-Modal Facility.

  • Is it possible to rent a car at LAX?

    If you want to rent a car once you land at LAX, you’ll be able to do so with ease since the airport features counters for Alamo, Avis, Fox, Enterprise, Budget, Dollar, Hertz, National, Payless, Six, Zipcar, and Thrifty. The counters for these agencies are housed in the airport’s car rental center, accessible through purple Rental Car Shuttles. These shuttles are boarded on the Lower/Arrivals Level islands outside the Baggage Claim.

  • How does KAYAK find such low prices on flights from Chicago to California?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to California.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to California?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to California is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to California?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly from Chicago to California with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to California?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to California up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding a cheap flight from Chicago to California

  • You can board your flight to California at Chicago Midway International Airport (MDW) or O’Hare International Airport (ORD). When selecting your flight, choose one that departs at MDW. Doing so is in your best interest because MDW experiences lower passenger traffic than ORD, meaning it has shorter queues.
  • When booking a flight to California, book one that lands at an airport close to your preferred destination. You can land at Los Angeles International Airport (LAX), San Diego International Airport (SAN), San Francisco International Airport (SFO), and Oakland International Airport (OAK) if you’re flying into Los Angeles, San Diego, San Francisco, and Oakland, respectively.
  • Suppose you intend to fly to California with your pet. If that’s the case, you can let your pet relieve itself at ORD in one of the airport’s Service Animal Relief Areas. They are outside security on the lower levels of Terminals 1, 2, and 5 and inside security in Terminal 3 Rotunda and Main Hall.
  • If a small airport serves your California destination, use LAX as your travel base. This is because it serves commercial flights to nearly all small airports in the state. If you need assistance at MDW, visit the airport’s information desk at the Main Entrance of the Terminal. Here, you’ll find knowledgeable airport staff, always ready to help.
  • If you need assistance at MDW, visit the airport’s information desk at the Main Entrance of the Terminal. Here, you’ll find knowledgeable airport staff, always ready to help.

More options for your flight from Chicago to California

Complete your trip to California with a hotel stay or car hire