$185 Cheap Flights from Appleton (ATW) to Chicago (MDW)

View $185 flight on Sat, Sep 13, 2025Opens in a new window

Popular airlines from Appleton, WI (ATW-Appleton Intl.) to Chicago Midway Airport (MDW)

Cheap Flights from Appleton to Chicago (ATW-MDW)

Prices were available within the past 7 days and start at $185 for one-way flights and $199 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Aug 12 - Mon, Aug 25
ATW
Appleton
MDW
Chicago
$199 Roundtrip, found 21 hours ago
$199
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Aug 12 from Appleton to Chicago, returning Mon, Aug 25, priced at $199 found 21 hours ago
Delta
Sat, Jun 28 - Tue, Jul 8
ATW
Appleton
MDW
Chicago
$204 Roundtrip, found 2 days ago
$204
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Jun 28 from Appleton to Chicago, returning Tue, Jul 8, priced at $204 found 2 days ago
Delta
Sat, Aug 16 - Sat, Aug 30
ATW
Appleton
MDW
Chicago
$204 Roundtrip, found 3 days ago
$204
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Aug 16 from Appleton to Chicago, returning Sat, Aug 30, priced at $204 found 3 days ago
Delta
Sat, Jun 28 - Sat, Jul 5
ATW
Appleton
MDW
Chicago
$209 Roundtrip, found 2 days ago
$209
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Jun 28 from Appleton to Chicago, returning Sat, Jul 5, priced at $209 found 2 days ago
Delta
Sat, Jun 21 - Tue, Jul 8
ATW
Appleton
MDW
Chicago
$214 Roundtrip, found 3 days ago
$214
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Jun 21 from Appleton to Chicago, returning Tue, Jul 8, priced at $214 found 3 days ago
Delta
Sat, Jun 21 - Sat, Jul 5
ATW
Appleton
MDW
Chicago
$219 Roundtrip, found 3 days ago
$219
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Jun 21 from Appleton to Chicago, returning Sat, Jul 5, priced at $219 found 3 days ago
Delta
Tue, Aug 12 - Tue, Aug 19
ATW
Appleton
MDW
Chicago
$232 Roundtrip, found 21 hours ago
$232
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Aug 12 from Appleton to Chicago, returning Tue, Aug 19, priced at $232 found 21 hours ago
Delta
Tue, Aug 12 - Wed, Aug 20
ATW
Appleton
MDW
Chicago
$239 Roundtrip, found 21 hours ago
$239
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Aug 12 from Appleton to Chicago, returning Wed, Aug 20, priced at $239 found 21 hours ago
Delta
Mon, Sep 1 - Tue, Sep 16
ATW
Appleton
MDW
Chicago
$242 Roundtrip, found 3 days ago
$242
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Sep 1 from Appleton to Chicago, returning Tue, Sep 16, priced at $242 found 3 days ago
Delta
Sat, Aug 30 - Sat, Sep 13
ATW
Appleton
MDW
Chicago
$244 Roundtrip, found 3 days ago
$244
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Aug 30 from Appleton to Chicago, returning Sat, Sep 13, priced at $244 found 3 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $234
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $234
Flights from Appleton (ATW) to Chicago (MDW)
Origin airport
Appleton Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$198
Distance
175 mi

Appleton to Chicago Flights

The cheapest times to fly from Appleton 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 Appleton to Chicago are during the month of August. You can find some of the cheapest flights from Appleton to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Appleton to Chicago

Sunday is one of the best days to book for cheap flights from Appleton 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 Appleton 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 Appleton to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $185 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 Appleton 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 Appleton 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 Appleton Intl. Airport (ATW) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from ATW to MDW 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 ATW to MDW?
The cheapest flights from ATW to MDW 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 ATW to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from ATW to MDW. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Appleton Intl. Airport (ATW) to Midway Intl. Airport (MDW)?
You’ll have to take a flight with a layover if you’re traveling from Appleton Intl. Airport (ATW) to Midway Intl. Airport (MDW). There are no daily direct flights on this route. However, just filter your search to include one or two stops to discover an option that works for you.
What day of the week has the most flights from ATW to MDW?
You’ll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Appleton Intl. Airport (ATW) to Midway Intl. Airport (MDW)?
To land at Midway Intl. Airport (MDW) on time, select a flight that leaves Appleton Intl. Airport (ATW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**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 Chicago from Appleton Intl. Airport (ATW)?
Browse your flight options from Appleton Intl. Airport (ATW) to O’Hare Intl. Airport (ORD). This is the only Chicago airport you can touch down at if you’re taking a direct flight.
Is it cheaper to buy a plane ticket from Appleton Intl. Airport (ATW) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from ATW to MDW are usually more expensive. For the lowest rates, start looking for flights early. That being said, if your travel plans are flexible, it’s possible to land a cheap ticket right before your journey.
Is it cheaper to book an ATW to MDW flight and hotel package?
You’ll typically save money by securing an ATW to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it’s easy to manage it all in one convenient place. Once you’ve chosen your ideal accommodations and flights, consider adding extras including car rentals, tours and activities.
Can I cancel or change the date of my flight from Appleton Intl. Airport (ATW) to Midway Intl. Airport (MDW)?
Generally, it’s possible to reschedule or cancel your ATW to MDW flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Check 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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*Available to One Key members.