$173 Cheap Flights from Rochester (ROC) to Chicago (MDW)
Popular airlines from Greater Rochester Intl. Airport (ROC) to Chicago Midway Airport (MDW)
DeltaDelta
Southwest AirlinesSouthwest Airlines
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Cheap Flights from Rochester to Chicago (ROC-MDW)
Alternative airports near Chicago
Prices were available within the past 7 days. Prices and availability are subject to change.
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Rochester (ROC) to Chicago (MDW) at a glance
Travel from Rochester (ROC) to Chicago (MDW) with a range of airlines catering to this domestic short-haul route. Discover options for cheap flights from Rochester and compare itineraries from both full-service and low-cost carriers to find the best fit for your budget and schedule. As you plan your trip to explore Chicago's iconic attractions and vibrant neighborhoods, gather essential information about flights from Greater Rochester International Airport to Midway International Airport.
- Fastest flight duration: around 2 hours non-stop
- Route distance: roughly 500 miles (800 km)
- Flights per week: around 7 departures on average
- Typical fares (one-way): economy tickets often range from $110–$295, depending on seasonality and how far ahead you book
Flights from Greater Rochester International Airport (ROC) to Midway International Airport (MDW)
Based on the latest traveler bookings, here are the top airlines favored for flights from Rochester to Chicago, primarily for non-stop and one-stop options. Many travelers opt for layovers at Detroit Metropolitan Wayne County Airport (DTW, about 45 minutes), Baltimore Washington International Thurgood Marshall Airport (BWI, approximately 2 hours and 45 minutes), and Hartsfield-Jackson Atlanta International Airport (ATL, around 1-hour layover). This flexibility allows you to compare prices, total travel time, and cabin classes to find the perfect itinerary.
- Southwest Airlines: Known for its budget-friendly fares, this low-cost airline provides both non-stop and one-stop options. One-way ticket prices generally fall between $110 and $295, making up about 85% of departures on this route, with a standard non-stop flight duration of 2 hours.
- Delta: As a full-service airline, Delta offers one-stop flights, with one-way fares typically ranging from $135 to $340. It represents roughly 15% of departures on this route, featuring an in-air time of 3 hours and 15 minutes, with a total travel duration of approximately 4 hours and 30 minutes, including layover time.
Alternative route from Rochester (ROC) to Chicago (MDW)
- Rochester to Chicago (ROC-ORD): O'Hare International Airport (ORD) is located roughly 16 miles from Midway International Airport (MDW). One-way economy prices for this route generally range from $100 to $315, influenced by the season and how far in advance you book. Travelers can choose between non-stop and one-stop flights, with major airlines such as American Airlines and United operating on this route. Additionally, first class service is offered for those seeking a more premium experience.
How to find the best prices for flights from Rochester (ROC) to Chicago (MDW)
Getting some of the best deals on flights from Rochester to Chicago is all about timing and flexibility. Here are some key tips to help you save:
- Best times to book and fly: cheaper fares are usually found when booking 2-8 weeks in advance, which coincides with when most travelers make their reservations. Afternoon departures from 12 PM to 6 PM often offer lower prices, although morning flights from 5 AM to 12 PM are the most popular. Additionally, flying on Saturday typically results in cheaper fares, while Friday is the busiest travel day.
- Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
- Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
- Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
- Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
- Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.
*Members only. Savings vary and are not available on all bundles. Select hotels.
Arriving at Midway International Airport from Greater Rochester International Airport
Chicago welcomes travelers from Rochester with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:
- Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
- Car rental: Renting a car from Midway International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Midway International Airport on Expedia.
- Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
- Public transportation: From Midway International Airport, travelers can easily access various transport options. Midway Station, a metro station, is located about 0.2 miles away on foot, while Chicago Ashburn Station, a train station, is about 4.1 miles from the airport by car. For those heading to the waterfront, Lyons Seaport, a seaport, is situated approximately 7.2 miles away by car.
Rochester to Chicago Flights
The cheapest times to fly from Rochester 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 Rochester to Chicago are during the month of November. You can find some of the cheapest flights from Rochester to Chicago with Expedia's search tool and vast selection of airlines.
The best time to book a flight from Rochester to Chicago
Sunday is one of the best days to book for cheap flights from Rochester 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 Rochester 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 Rochester to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $173 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 Rochester 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 Rochester 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 Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $173 and cheap return flights $311 Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights generally range between $205 and $631, and roundtrip flights usually range from $342 to $780. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.) ticket fares go up or down.
*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from ROC to MDW is November when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter ROC to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.)?
Southwest Airlines is one of the cheapest airlines offering nonstop flights from Greater Rochester Intl. (ROC) to Midway Intl. (MDW), with round-trip tickets starting from around $279.97. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best airline to fly with from Rochester, NY (ROC) to Chicago, IL (MDW) will differ from traveler to traveler. If you like to fly early, WN offers early morning flights. If price is the most important factor, WN typically offers the lowest fares. WN offers the most daily flights from ROC to MDW, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.)?
On average, there are around 2 nonstop flights per day from Greater Rochester Intl. (ROC) to Midway Intl. (MDW). For more options, look at flights that include layovers.
What is the earliest flight from Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Greater Rochester International Airport (ROC) to Midway International Airport (MDW) typically departs at around 5:20 AM, operated by Southwest Airlines. This seasonal service can help you start your day early and maximize your time in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Rochester, NY (ROC) to Chicago, IL (MDW) are in the early morning, from 6am to 9am. About 35% of passengers prefer this time window. Many major carriers, including Southwest Airlines and Delta Airlines, offer flights during this window. This timing is popular because it allows you to maximize your day in Chicago upon arrival.
How long does it take to fly from Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.)?
A nonstop flight from ROC to MDW typically takes around 1 hour 50 minutes, covering approximately 522 miles. Connecting flights on this route usually add 5 hours 10 minutes to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.)?
First class seats are offered on the ROC to MDW route with Delta Air Lines.
How do I earn miles on a Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.
*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Greater Rochester Intl. (ROC)?
When traveling from Greater Rochester Intl. (ROC) to Chicago, you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD). Some flights may connect through major hubs like Baltimore Washington Intl. Thurgood Marshall (BWI), Washington Dulles Intl. (IAD), Liberty Intl. (EWR) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Rochester, NY (ROC-Greater Rochester Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.
Travel information
Origin airport | Greater Rochester Intl. Airport |
|---|---|
Destination airport | Chicago Midway Airport |
Distance | 521 miles away |
Airlines serving | Delta, Southwest Airlines |
Popular airline | Delta |
Roundtrip price | $311 |
Average flight time | 1 hour 50 mins |