Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

Cheap Flight Deals From Gainesville (JAX) to Chicago (CHI) Starting at $43

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This Weekend's Flight Deals from Gainesville to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $43 One Way, $68 Round Trip from Gainesville to Chicago

Prices starting at $68 for return flights and $43 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Chicago economy flight packages

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Park Hyatt Chicago
Courtyard by Marriott Chicago Downtown River North
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More About Flying To Chicago from Gainesville

Route Information for Flights from Gainesville to Chicago

Origin Airport IATA Code JAX
Destination Airport IATA Code CHI
Distance 1006 mi
Direct Flight Airlines American Airlines, Qatar Airways, JAL, Air Canada, LOT - Polish Airlines, Austrian, Copa Airlines, SWISS, Air New Zealand, United Airlines, Alaska Airlines, Frontier Airlines, Southwest Airlines, SAS, Royal Jordanian, Iberia, ANA, Lufthansa, Spirit Airlines, British Airways
Earliest Flight Arrival 12:30PM UTC
Latest Flight Arrival 3:44AM UTC

Cheap Flights from Gainesville to Chicago

Gainesville Airport Information

Whether you are a University of Florida student headed home or simply embarking on a vacation adventure, Orbitz.com can help you find cheap flights from Gainesville. You take off from the Gainesville Regional Airport, which is served by American Airlines, American Eagle, Delta, United and US Airways. You might be tempted to fly out of one of the area's larger airports, but you would then face a 120-mile drive to the Orlando International Airport or an 80-mile drive to the Jacksonville International Airport before you even start your trip.

Airport Parking in Gainesville

The Gainesville Regional Airport has plenty of available parking just a short walk from the terminal. The short-term lot charges up to $12 per day, while the long-term lot charges $9 per day or $55 per week. There are also several off-site parking facilities that offer free shuttle service to and from the airport. Check your vacation planner with Orbitz.com before you leave to make sure you have chosen the best parking option based on the length of your trip to help you stay within your budget.

Ground Transportation in Gainesville

The Regional Transit Bus Service (RTS) is the most economical way to get to the Gainesville airport. University of Florida students can also pick up the route #25 bus on Monday through Friday. There are several taxi companies that offer transportation to the airport, but if you purchased your air tickets through Orbitz.com, you may have saved enough to warrant splurging on a private car service to get you to the airport in style.

Restaurants in Gainesville

The Gainesville airport has dedicated amenities to serve business and leisure travelers, including Wi-Fi and an ATM, but dining opportunities are limited. Tailwind has a full-service restaurant and bar in the public area before the security checkpoint, but within the terminal, options are more limited. There is a full-service bar in the gate area, but the only food available is grab-and-go snacks. Enjoy your trip, wherever your travels take you, and remember to use Orbitz.com the next time you need to find cheap flights from Gainesville.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Flights from Gainesville to Chicago - Frequently Asked Questions

Am I able to catch a flight from Gainesville to Chicago now?

Head to our Covid-19 Travel Advisor for the most useful information on travel restrictions and quarantine requirements when catching a flight from Gainesville to Chicago.

Are there non-stop flights from Gainesville to Chicago?

No less than 4 airlines offer nonstop services from Orlando, FL Airport (MCO-Orlando Intl.) to O'Hare Airport, so you don't have to worry about switching planes or missing your connecting flight. Sought-after carriers on this route include:

  • American Airlines
  • United Airlines
  • Spirit Airlines
  • Frontier Airlines
What is the shortest flight from Gainesville to Chicago?

If conditions are good and there are no unexpected hiccups, you could be coming in to land at O'Hare Airport from Orlando Intl. Airport (MCO) in as little as 2 hours and 50 minutes. With such a short flight time, contemplate bringing just carry-on luggage.

What airlines fly from Gainesville to Chicago most frequently?

We all have our preferences when it comes to airlines, and you have a nice variety when jetting off from Gainesville to Chicago. These leading carriers fly this route most frequently: American Airlines - (AA) with 147 flights every month United Airlines - (UA) with 147 flights every month Spirit Airlines - (NK) with 65 flights every month Frontier Airlines - (F9) with 30 flights every month

If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Chicago with flexible change policies?

In most cases you'll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2020 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2020 saved up to 45% on their airfares. Get mixing and matching today!

*According to flight demand on Orbitz.com from January to December 2020. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.