Title: Cheap flights from Ocala to Chicago (OCF to PWK) - Expedia.com ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap Flights from Ocala (OCF) to Chicago (PWK) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travelers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only ## Popular airlines from Ocala, FL (OCF-Ocala Intl.) to Chicago, IL (PWK-Chicago Executive) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.com/Flights-Search?leg1=from:OCF,to:PWK,departure:2/19/2026TANYT&leg2=from:PWK,to:OCF,departure:2/26/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.com/Flights-Search?leg1=from:OCF,to:PWK,departure:2/19/2026TANYT&leg2=from:PWK,to:OCF,departure:2/26/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.com/Flights-Search?leg1=from:OCF,to:PWK,departure:2/19/2026TANYT&leg2=from:PWK,to:OCF,departure:2/26/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:OCF,to:PWK,departure:2/19/2026TANYT&leg2=from:PWK,to:OCF,departure:2/26/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.com/Flights-Search?leg1=from:OCF,to:PWK,departure:2/19/2026TANYT&leg2=from:PWK,to:OCF,departure:2/26/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.com/Flights-Search?leg1=from:OCF,to:PWK,departure:2/19/2026TANYT&leg2=from:PWK,to:OCF,departure:2/26/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.com/Flights-Search?leg1=from:OCF,to:PWK,departure:2/19/2026TANYT&leg2=from:PWK,to:OCF,departure:2/26/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our OneKeyCash [Learn about One Key](https://www.expedia.com/welcome-one-key) __Flights from Ocala (OCF) to Chicago (PWK)__ | Origin airport | Ocala Intl. | | ------------------- | ----------------- | | Destination airport | Chicago Executive | | Distance | 948 mi | ## Ocala to Chicago Flights The cheapest times to fly from Ocala 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 Ocala to Chicago are during the month of . You can find some of the cheapest flights from Ocala to Chicago with Expedia's search tool and vast selection of airlines. The best time to book a flight from Ocala to Chicago Sunday is one of the best days to book for cheap flights from Ocala 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 Ocala 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 Ocala to Chicago in 2026\. You can also book with separate airlines for your outbound and return journeys, from 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 Ocala 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](https://www.expedia.com/package-deals). Bundling together your Ocala 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 ### How much does a flight from Ocala, FL (OCF-Ocala Intl.) to Chicago Executive Airport (PWK) cost? ### What is the cheapest month to fly from Ocala, FL (OCF-Ocala Intl.) to Chicago Executive Airport (PWK)? ### What is the cheapest airline that flies from Ocala, FL (OCF-Ocala Intl.) to Chicago Executive Airport (PWK)? ### How many flights per day from Ocala, FL (OCF-Ocala Intl.) to Chicago Executive Airport (PWK)? ### What day of the week has the most flights from OCF to PWK? ### What is the best time to fly from Ocala, FL (OCF-Ocala Intl.) to Chicago Executive Airport (PWK)? ### Is it cheaper to buy a plane ticket from Ocala, FL (OCF-Ocala Intl.) to Chicago Executive Airport (PWK) last-minute? ### Is it cheaper to book an OCF to PWK flight and hotel package? ### Can I cancel or change the date of my flight from Ocala, FL (OCF-Ocala Intl.) to Chicago Executive Airport (PWK)? \*Flight schedules are subject to change. ## Explore a world of travel with Expedia - 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