C$297 Cheap Flights from Indianapolis to Chicago Midway

Compare Indianapolis 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 Indianapolis to Chicago Midway

Looking for a cheap last-minute deal or the best round-trip flight from Indianapolis to Chicago Midway? Find the lowest prices on one-way and round-trip tickets right here.

Chicago.C$297 per passenger.Departing Thu, Sep 11, returning Mon, Sep 15.Round-trip flight with Spirit Airlines and Frontier Airlines.Outbound indirect flight with Spirit Airlines, departing from Indianapolis on Thu, Sep 11, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Mon, Sep 15, arriving in Indianapolis.Price includes taxes and charges.From C$297, select.

Chicago.C$299 per passenger.Departing Sat, Dec 13, returning Sat, Dec 13.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Indianapolis on Sat, Dec 13, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Sat, Dec 13, arriving in Indianapolis.Price includes taxes and charges.From C$299, select.

Chicago.C$299 per passenger.Departing Thu, Oct 23, returning Mon, Oct 27.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Indianapolis on Thu, Oct 23, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Mon, Oct 27, arriving in Indianapolis.Price includes taxes and charges.From C$299, select.

Chicago.C$299 per passenger.Departing Thu, Sep 18, returning Thu, Sep 18.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Indianapolis on Thu, Sep 18, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Thu, Sep 18, arriving in Indianapolis.Price includes taxes and charges.From C$299, select.

Chicago.C$303 per passenger.Departing Wed, Nov 26, returning Tue, Dec 2.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Indianapolis on Wed, Nov 26, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Tue, Dec 2, arriving in Indianapolis.Price includes taxes and charges.From C$303, select.

Chicago.C$304 per passenger.Departing Wed, Nov 5, returning Fri, Nov 7.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Indianapolis on Wed, Nov 5, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Fri, Nov 7, arriving in Indianapolis.Price includes taxes and charges.From C$304, select.

Chicago.C$316 per passenger.Departing Sun, Aug 31, returning Thu, Sep 18.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Indianapolis on Sun, Aug 31, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Thu, Sep 18, arriving in Indianapolis.Price includes taxes and charges.From C$316, select.

Chicago.C$330 per passenger.Departing Thu, Oct 30, returning Sun, Nov 2.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Indianapolis on Thu, Oct 30, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Sun, Nov 2, arriving in Indianapolis.Price includes taxes and charges.From C$330, select.

Find the cheapest month to fly from Indianapolis to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Indianapolis to Chicago Midway flights are currently cheapest in September.

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Mar

Apr

May

Jun

Jul

Which airlines fly from Indianapolis to Chicago Midway?

Indianapolis to Chicago Midway: Alternative routes

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

Indianapolis to Chicago: Flight information

The things to know before you go.

Cheapest flight found	C$299
Cheapest month to fly	September
Average flight time	1 hr, 6 mins
Most popular airline	Southwest Airlines
Average flights per week	13

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

How much are round-trip flights from Indianapolis to Chicago Midway?

The best price we found for a round-trip flight from Indianapolis to Chicago Midway is C$297. 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 Indianapolis to Chicago Midway?

1 hour and 6 minutes is the average flight time from Indianapolis to Chicago Midway.

Which airlines fly direct from Indianapolis to Chicago Midway?

Southwest Airlines flies direct from Indianapolis to Chicago Midway.

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

There are 13 flights per week flying from Indianapolis to Chicago Midway, as of August 2025.

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

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

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

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Indianapolis Airport to Chicago Midway Airport on Thursday, September 11, 2025.

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

Yes – the average flight time is 1 hour and 6 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 with from Indianapolis Airport to Chicago Midway?

Currently, Spirit Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

Flying from Indianapolis International Airport (IND) to Chicago Midway International Airport (MDW): what you need to know

Chicago is one hour behind Indianapolis and observes the UTC-5 timezone.
Get to the airport on time so you don't miss your IND to MDW flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid the stress of rushing.
Be prepared for longer lines during popular months such as July. Arriving up to four hours in advance for an international flight and two hours for domestic departures is a good idea.
We make it simple to book a flight with a stopover. To see your options for tickets from Indianapolis International Airport to Chicago Midway International Airport, deselect 'Direct flights only.' Then, pick a flight with a stop long enough to explore your chosen city. Popular stopovers between IND and MDW include:
- Detroit Metropolitan Wayne County Airport
- Hartsfield-Jackson Atlanta International Airport
- Baltimore/Wash International Thurgood Marshall Airport

How to find the cheapest flights from Indianapolis International Airport (IND) to Chicago Midway International Airport (MDW)

Right now, C$135 is the lowest price we've seen for a one-way Indianapolis International Airport to Chicago Midway International Airport flight. The best price for a return plane ticket is C$297. Bear in mind that fares can change due to availability at the time of booking.
It's usually smart to book early if you want to find cheap tickets from IND to MDW. That's because flight prices are based on demand, which tends to increase closer to departure.
If you're willing to be flexible with your travel dates, use the 'Whole month' tool. It'll find the cheapest price across every month when searching for your flight from Indianapolis International Airport to Chicago Midway International Airport.
You won't have to check back in every day to see if fares have dropped when you create a Price Alert. We'll update you the moment there's a better deal on cheap flights from IND to MDW.
Tailor your trip using filters. Pick your ideal departure and arrival times, total journey duration and airlines. You can also sort your results by 'Cheapest,' 'Fastest' or 'Best' flights from Indianapolis International Airport to Chicago Midway International Airport.

Handy information about Indianapolis International Airport (IND)

IND is located at 7800 Col. H. Weir Cook Memorial Drive.
When it comes to Indianapolis International Airport's on-time performance, 79.86% of flights complete their journey on time.
To reach Indianapolis International Airport from central Indianapolis, it'll take about 25 minutes if you're planning to drive. Of course, this depends on traffic. It's approximately 24 kilometres from the airport to the city centre.
You can expect a journey time of around 1 hour on public transport.
Taking an early flight from Indianapolis International Airport to Chicago Midway International Airport? Avoid rushing to the terminal (and enjoy a little extra shut-eye) by choosing one of these hotels near IND:

Arriving at Chicago Midway International Airport (MDW)

Reserve a hotel close to MDW if you have a late Indianapolis International Airport to Chicago Midway International Airport flight. Settle into one of these accommodation options and make your arrival easier:
Grab a Chicago Midway International Airport rental car and explore Chicago and beyond with your own wheels. Dollar, Hertz and Budget are top providers to choose from here.
Booking your vehicle from Chicago Midway International Airport about four weeks ahead can help you get the lowest rate.

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

MDW is located at 5700 South Cicero.
From Chicago Midway International Airport, Chicago is approximately 19 kilometres away. It takes around 20 minutes to reach the centre driving.
It'll take around 45 minutes if you're using public transport.

When to fly to Chicago Midway International Airport (MDW)

July is the busiest month for flights from Indianapolis International Airport to Chicago Midway International Airport. For a quieter experience, visit Chicago in May.
Lock in your flight from Indianapolis International Airport to Chicago Midway International Airport for July if you'd like to go to Chicago during its warmest month. Expect temperatures of between 15ºC (59ºF) and 29ºC (84ºF).
Look for cheap tickets from IND to MDW in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

Explore more of United States

You've done Chicago, now it's time to explore other corners of United States. Journey around 451 kilometres south-east to Columbus to tick off its top attractions. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you'll have a full itinerary ahead.
Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in United States. Get a taste of what this destination has to offer at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.