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Cheap Flights from Rochester (ROC) to Chicago (MDW)

Compare Rochester to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Rochester to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Rochester to Chicago Midway? Find the lowest prices on one-way and return tickets right here.
Chicago.$331 per passenger.Departing Wed, 27 Aug, returning Sat, 30 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Rochester on Wed, 27 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 30 Aug, arriving in Rochester.Price includes taxes and charges.From $331, select.
Chicago.$384 per passenger.Departing Sat, 30 Aug, returning Mon, 1 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Rochester on Sat, 30 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 1 Sep, arriving in Rochester.Price includes taxes and charges.From $384, select.
Chicago.$449 per passenger.Departing Fri, 31 Oct, returning Sat, 8 Nov.Return flight with Delta.Outbound indirect flight with Delta, departs from Rochester on Fri, 31 Oct, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sat, 8 Nov, arriving in Rochester.Price includes taxes and charges.From $449, select.
Chicago.$449 per passenger.Departing Wed, 17 Sep, returning Sun, 21 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Rochester on Wed, 17 Sep, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sun, 21 Sep, arriving in Rochester.Price includes taxes and charges.From $449, select.
Chicago.$508 per passenger.Departing Fri, 5 Sep, returning Sun, 7 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Rochester on Fri, 5 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 7 Sep, arriving in Rochester.Price includes taxes and charges.From $508, select.
Chicago.$536 per passenger.Departing Fri, 3 Oct, returning Sun, 5 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Rochester on Fri, 3 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 5 Oct, arriving in Rochester.Price includes taxes and charges.From $536, select.
Chicago.$565 per passenger.Departing Fri, 21 Nov, returning Sun, 23 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Rochester on Fri, 21 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 23 Nov, arriving in Rochester.Price includes taxes and charges.From $565, select.
Chicago.$617 per passenger.Departing Wed, 30 Jul, returning Sat, 2 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Rochester on Wed, 30 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 2 Aug, arriving in Rochester.Price includes taxes and charges.From $617, select.

Find the cheapest month to fly from Rochester to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Rochester to Chicago Midway flights are currently cheapest in August.
Jul
from $658
Aug
from $331
Sep
from $449
Oct
from $536
Nov
from $565
Dec
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Jan
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Feb
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Mar
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Apr
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May
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Jun
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Direct flights from Rochester to Chicago Midway

Rochester to Chicago Midway: Alternative routes

Compare routes from Rochester to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Rochester to Chicago: Flight information

The things to know before you go.
Cheapest flight found$331
Cheapest month to flyAugust
Average flight time1 hr, 54 mins
Most popular airlineSouthwest Airlines
Average flights per week8

Finding cheap flights from Rochester to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Rochester to Chicago Midway is $331. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
1 hour and 54 minutes is the average flight time from Rochester to Chicago Midway.
Southwest Airlines flies direct from Rochester to Chicago Midway.
As of July 2025, there are 8 flights per week flying from Rochester to Chicago Midway.
The cheapest month to fly from Rochester to Chicago Midway is usually August.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Rochester Airport to Chicago Midway Airport on Wednesday, 27 August 2025.
Yes – the average flight time is 1 hour and 54 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

Travelling from Greater Rochester International Airport (ROC) to Chicago Midway International Airport (MDW): what you need to know

  • The average duration of a direct flight from Greater Rochester International Airport to Chicago Midway International Airport is 1 hour 45 minutes.

  • Chicago is one hour behind Rochester and is in the UTC-5 timezone.

  • Choose from five weekly Greater Rochester International Airport to Chicago Midway International Airport flights. The 06:20 departure with Southwest Airlines is the earliest flight you can take. Southwest Airlines operates the last service of the day at 20:45.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for hassle-free flying. Get to the airport on time to board your ROC to MDW flight.

  • You can expect bigger queues in popular months like August. Arriving up to four hours in advance for international flights and two hours for domestic departures is a smart move.

  • Southwest Airlines offers direct flights from Greater Rochester International Airport to Chicago Midway International Airport. Book with this popular carrier, then get ready to discover the sights in Chicago — and maybe even more of United States if you have time.

  • Southwest Airlines is the airline with the highest passenger demand for this route.

  • If you want to explore another city along the way, simply uncheck 'Direct flights only' when searching for your ticket from Greater Rochester International Airport to Chicago Midway International Airport. These are the top stopovers between ROC and MDW:

    • Detroit Metropolitan Wayne County Airport

    • Baltimore/Wash International Thurgood Marshall Airport

    • Philadelphia International Airport

How to find the cheapest flights from Greater Rochester International Airport (ROC) to Chicago Midway International Airport (MDW)

  • The lowest price we've seen for a one-way Greater Rochester International Airport to Chicago Midway International Airport flight is $165. A return ticket is currently $331. Depending on the availability and when you book, these fares may change.

  • To get cheap tickets from ROC to MDW, reserve your trip six months ahead of your departure date.

  • Schedule your trip for May. That's the cheapest month for flights from Greater Rochester International Airport to Chicago Midway International Airport. If your travel dates are flexible, use the 'Whole month' tool to see the cheapest price across each month.

  • You don't need to check every day to find out if fares have dropped when you create a Price Alert. We'll notify you as soon as a special offer becomes available on cheap flights from ROC to MDW.

  • Find the perfect flight for you by using the filters. To see the 'Best,' 'Cheapest' or 'Fastest' flights from Greater Rochester International Airport to Chicago Midway International Airport, use the 'Sort by' tool. You can also filter results by departure and arrival times, airline, and number of stops.

Handy information about Greater Rochester International Airport (ROC)

  • ROC is located at 1200 Brooks Avenue.

  • Of all flights leaving Greater Rochester International Airport, 73.76% land on schedule at their destination.

  • To get to Greater Rochester International Airport from central Rochester, it takes around 15 minutes if you're going by car. This depends on traffic, however. It's approximately 13 kilometres from the airport to the city centre.

  • You can expect a journey time of about 1 hour 35 minutes on public transport.

  • Need a convenient hotel near ROC? If you're catching an early flight from Greater Rochester International Airport to Chicago Midway International Airport, these accommodation options will have you sleeping moments from your departure lounge:

Arriving at Chicago Midway International Airport (MDW)

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • You'll find MDW at 5700 South Cicero.

  • From Chicago Midway International Airport, Chicago is approximately 19 kilometres away. It takes around 20 minutes to reach the centre by car.

  • If you're using public transport, expect a journey of about 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • The quietest month for a flight from Greater Rochester International Airport to Chicago Midway International Airport is May, while July is the most popular. Pick the best time to go to Chicago based on whether you prefer a bustling atmosphere or a more laid-back vibe.

  • The warmest month in Chicago is July, with the temperature ranging between 15ºC (59ºF) and 29ºC (84ºF). Book your flights from Greater Rochester International Airport to Chicago Midway International Airport in this month if this is the type of weather you enjoy.

  • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for cheap tickets from ROC to MDW around that time if you'd rather travel in cooler conditions.

Explore more of United States

  • Columbus is just one of the many cities in United States waiting to be explored once you've seen Chicago. Around 451 kilometres away to the south-east, its best attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • If there's time to check out another major destination in United States, head for Indianapolis, roughly 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are the start of reasons to visit.

Plan the rest of your trip from Rochester to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.