Cheap Flights from Rochester to Chicago Midway from $505

Compare Rochester to Chicago Midway flight deals

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

Book the best Chicago Midway fare with no extra fees

Flight deals from Rochester to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Rochester Airport to Chicago Midway Airport? If you want to travel next month, return fares start from $633. Find the lowest prices on one-way and return tickets right here.

Chicago.$505 per passenger.Departing Sat, 12 Sep, returning Tue, 15 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Rochester on Sat, 12 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 15 Sep, arriving in Rochester.Price includes taxes and charges.From $505, select.

Chicago.$506 per passenger.Departing Wed, 5 Aug, returning Tue, 11 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Rochester on Wed, 5 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 11 Aug, arriving in Rochester.Price includes taxes and charges.From $506, select.

Chicago.$564 per passenger.Departing Thu, 15 Oct, returning Thu, 22 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Rochester on Thu, 15 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 22 Oct, arriving in Rochester.Price includes taxes and charges.From $564, select.

Chicago.$564 per passenger.Departing Thu, 12 Nov, returning Mon, 16 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Rochester on Thu, 12 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 16 Nov, arriving in Rochester.Price includes taxes and charges.From $564, select.

Chicago.$613 per passenger.Departing Tue, 1 Dec, returning Fri, 8 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Rochester on Tue, 1 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 8 Jan, arriving in Rochester.Price includes taxes and charges.From $613, select.

Chicago.$633 per passenger.Departing Wed, 15 Jul, returning Sun, 19 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Rochester on Wed, 15 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 19 Jul, arriving in Rochester.Price includes taxes and charges.From $633, select.

Chicago.$728 per passenger.Departing Wed, 10 Feb, returning Wed, 24 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Rochester on Wed, 10 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 24 Feb, arriving in Rochester.Price includes taxes and charges.From $728, select.

Chicago.$729 per passenger.Departing Fri, 10 Jul, returning Thu, 3 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Rochester on Fri, 10 Jul, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 3 Sep, arriving in Rochester.Price includes taxes and charges.From $729, select.

Chicago.$745 per passenger.Departing Mon, 27 Jul, returning Mon, 3 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Rochester on Mon, 27 Jul, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 3 Aug, arriving in Rochester.Price includes taxes and charges.From $745, select.

Chicago.$1,064 per passenger.Departing Mon, 29 Jun, returning Tue, 30 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Rochester on Mon, 29 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 30 Jun, arriving in Rochester.Price includes taxes and charges.From $1,064, select.

Chicago.$1,123 per passenger.Departing Mon, 29 Jun, returning Sun, 5 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Rochester on Mon, 29 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 5 Jul, arriving in Rochester.Price includes taxes and charges.From $1,123, 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 September.

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Mar

Apr

May

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	$505
Cheapest month to fly	September
Average flight time	1 hr, 54 mins
Most popular airline	Southwest Airlines
Average flights per week	14

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

How much are return flights from Rochester to Chicago Midway?

The best price we found for a return flight from Rochester to Chicago Midway is $505. 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.

How long does it take to fly from Rochester to Chicago Midway?

1 hour and 54 minutes is the average flight time from Rochester to Chicago Midway.

Which airlines fly direct from Rochester to Chicago Midway?

Southwest Airlines flies direct from Rochester to Chicago Midway.

How many flights are there a week from Rochester to Chicago Midway?

As of June 2026, there are 14 flights per week flying from Rochester to Chicago Midway.

When is the cheapest time to fly from Rochester to Chicago Midway?

The cheapest month to fly from Rochester to Chicago Midway is usually September.

Which upcoming date is cheapest to fly from Rochester Airport to Chicago Midway Airport on?

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 Saturday, 12 September 2026.

Can I get a direct flight from Rochester Airport to Chicago Midway Airport?

Yes – the average flight time is 1 hour and 54 minutes.

How can I find the best flight deal to Chicago Midway?

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.

When is the best time to book flights to Chicago?

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.

Which is the cheapest airline to fly from Rochester Airport to Chicago Midway with?

Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

Flying from Rochester Airport (ROC) to Chicago Midway Airport (MDW): what you need to know

The average time for a direct flight from Rochester Airport to Chicago Midway Airport is 1 hour 45 minutes.
Chicago is one hour behind Rochester and is in the UTC-6 timezone.
Each week, there are eight Rochester Airport to Chicago Midway Airport flights. To be on board early, opt for the 06:25 Southwest Airlines flight. If you'd rather make the most of your day before flying, the last flight is at 20:10 with Southwest Airlines.
To ensure you get on your ROC to MDW flight, leave enough time for things like baggage drop and finding your gate. Arriving two hours before international departures and one hour before domestic flights is the general travel rule.
You'll likely experience bigger queues during popular months such as October. Arriving up to four hours in advance for an international flight and two hours for a domestic departure is a good idea.
Flying into Chicago (and then discovering more of the United States!) is a cinch with Southwest Airlines. This popular airline has direct flights from Rochester Airport to Chicago Midway Airport.
The majority of travellers choose to fly with Southwest Airlines on this route.
Southwest Airlines is a leader in on-time performance for ROC to MDW flights, with 83.64% of services arriving on schedule.
Think about adding a stopover when booking your ticket from Rochester Airport to Chicago Midway Airport. Just uncheck 'Direct flights only' to break up your journey, or enjoy a detour to a new and interesting place. Here are some options between ROC and MDW:
- Detroit Wayne County Airport
- Philadelphia International Airport
- Baltimore Washington International Airport

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

$251 is currently the lowest price for a one-way Rochester Airport to Chicago Midway Airport flight. Return flights start at $505. These prices may change depending on availability and demand.
Don't leave everything to the last minute. You're more likely to find cheap tickets from ROC to MDW if you book ahead. Airlines often have some excellent early bird deals.
Schedule your trip for May. That's the cheapest month for flights from Rochester Airport to Chicago Midway Airport. If you're flexible with your travel dates, use the 'Whole month' tool to see the lowest price across each month.
You won't have to check back in every day to find out if fares have gone down when you create a Price Alert. We'll update you the moment there's a better deal on cheap flights from ROC to MDW.
Choose your preferred departure and arrival times, airlines and number of stops with the filters. Or sort your results by 'Cheapest' to find the best deals on flights from Rochester Airport to Chicago Midway Airport.

Handy information about Rochester Airport (ROC)

You'll find ROC at 1200 Brooks Avenue.
When it comes to the on-time performance of Rochester Airport, data shows 72% of flights arrive within the scheduled timeframe.
Rochester Airport is about 11 kilometres from central Rochester. If you're driving, catching a taxi or ride-sharing from the centre, it'll take you 15 minutes or so to get there, depending on the traffic.
Expect a trip time of about 35 minutes on public transport.
Searching for a convenient hotel close to ROC? If you're boarding an early flight from Rochester Airport to Chicago Midway Airport, these stays will have you sleeping moments from check-in:

Arriving at Chicago Midway Airport (MDW)

The last thing you want is a lengthy journey to your hotel if you're arriving on a late Rochester Airport to Chicago Midway Airport flight. Check in to one of these accommodation options near MDW instead:
Pick up a Chicago Midway Airport rental car and discover Chicago and beyond with your own set of wheels. Dollar, Hertz and Budget are popular providers you can book with here.
Lock in the best possible rate by reserving your ride from Chicago Midway Airport around four weeks in advance of your trip.

Getting from Chicago Midway Airport (MDW) to central Chicago

You'll find MDW at 5700 South Cicero.
From Chicago Midway Airport, Chicago is approximately 16 kilometres away. It takes around 25 minutes to drive to the centre.
It typically takes 30 minutes if you're travelling on public transport.

When to fly to Chicago Midway Airport (MDW)

It's time to plan your trip dates for your flight from Rochester Airport to Chicago Midway Airport. July is the busiest month to visit Chicago. If you prefer a more laid-back vibe, go in December.
When reserving your flight from Rochester Airport to Chicago Midway Airport, consider the kind of weather you like. July is the warmest month in Chicago, with the temperature ranging from 16ºC to 28ºC.
January has average temperatures of between -12ºC and 3ºC. Look for cheap tickets from ROC to MDW sometime around then if you want to travel in cooler conditions.

Explore more of the United States

Chicago has plenty going for it, but there are so many other corners of the United States just waiting to be explored. Around 451 kilometres south-east of Chicago, a trip to Columbus will keep you on the move. Start with leading sights like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.
Indianapolis is another essential stop in the United States and is around 257 kilometres south-east of Chicago. No trip is complete without a visit to Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.