Cheap Flights from Chicago (MDW) to St. Augustine (UST)

Popular airlines from Chicago Midway Airport (MDW) to St. Augustine, FL (UST-Northeast Florida Regional)

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Find available prices by choosing your travel dates.
Flights from Chicago (MDW) to St. Augustine (UST)
Origin airport
Midway Intl.
Destination airport
Northeast Florida Regional
Distance
891 mi

Chicago to St. Augustine Flights

The cheapest times to fly from Chicago to St. Augustine

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 Chicago to St. Augustine are during the month of . You can find some of the cheapest flights from Chicago to St. Augustine with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to St. Augustine

Sunday is one of the best days to book for cheap flights from Chicago to St. Augustine: 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 Chicago to St. Augustine

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 Chicago to St. Augustine in 2025. 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 Chicago to St. Augustine 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 Chicago to St. Augustine 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 Midway Intl. Airport (MDW) to Northeast Florida Regional Airport (UST) cost?
Discover the latest flight deals from MDW to UST by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to UST?
The cheapest flights from MDW to UST are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from MDW to UST?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from MDW to UST. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Northeast Florida Regional Airport (UST)?
Direct flights from Midway Intl. Airport (MDW) to Northeast Florida Regional Airport (UST) aren’t available daily, so you’ll have to take a flight with a layover. Explore your options with Expedia’s filters. Enter your travel dates and pick either “1 Stop” or “2+ Stops.”
What day of the week has the most flights from MDW to UST?
Typically you’ll find the largest variety of flight choices on a Friday. Tuesdays are often the quietest.* However, this can vary based on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Northeast Florida Regional Airport (UST)?
Select a flight from Midway Intl. Airport (MDW) to Northeast Florida Regional Airport (UST) that leaves before 3 PM to reduce the risk of delays and cancellations. Departures later than this have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for St. Augustine from Midway Intl. Airport (MDW)?
Explore your flight options from Midway Intl. Airport (MDW) to Jacksonville Intl. Airport (JAX). This is the only St. Augustine airport you can land at if you’re taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Northeast Florida Regional Airport (UST) last-minute?
Booking your ticket from MDW to UST shortly before your trip is usually more expensive. However, if you’re flexible with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a MDW to UST flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to UST flight and hotel package with Expedia could lead to significant savings. What’s more, managing everything in one place takes the hassle out of planning your trip. Just secure your flights and select from our extensive range of hotels, then personalize your trip with other add-ons like car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Northeast Florida Regional Airport (UST)?
Usually, it’s possible to cancel or reschedule your MDW to UST flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline’s policies in your itinerary to see what changes are allowed and whether any costs are involved. You’ll also find further details on our Customer Service portal.

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