$89 Cheap Flights from Cincinnati (CVG) to Chicago (MDW)

View $89 flight on Sat, Aug 30, 2025Opens in a new window

Popular airlines from Cincinnati-Northern Kentucky Int'l Airport (CVG) to Chicago Midway Airport (MDW)

Cheap Flights from Cincinnati to Chicago (CVG-MDW)

Prices were available within the past 7 days and start at $89 for one-way flights and $177 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Sep 6 - Mon, Sep 8
CVG
Cincinnati
MDW
Chicago
$177 Roundtrip, found 11 hours ago
$177
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Sat, Sep 6 from Cincinnati to Chicago, returning Mon, Sep 8, priced at $177 found 11 hours ago
Frontier Airlines
Thu, Aug 21 - Mon, Aug 25
CVG
Cincinnati
MDW
Chicago
$183 Roundtrip, just found
$183
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Aug 21 from Cincinnati to Chicago, returning Mon, Aug 25, priced at $183 just found
Frontier Airlines
Mon, Aug 11 - Tue, Oct 7
CVG
Cincinnati
MDW
Chicago
$184 Roundtrip, found 4 days ago
$184
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Aug 11 from Cincinnati to Chicago, returning Tue, Oct 7, priced at $184 found 4 days ago
Southwest Airlines
Fri, Oct 3 - Mon, Oct 6
CVG
Cincinnati
MDW
Chicago
$186 Roundtrip, found 1 hour ago
$186
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Fri, Oct 3 from Cincinnati to Chicago, returning Mon, Oct 6, priced at $186 found 1 hour ago
Southwest Airlines
Wed, Oct 1 - Mon, Oct 6
CVG
Cincinnati
MDW
Chicago
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Oct 1 from Cincinnati to Chicago, returning Mon, Oct 6, priced at $187 found 1 day ago
Frontier Airlines
Thu, Nov 6 - Mon, Nov 10
CVG
Cincinnati
MDW
Chicago
$188 Roundtrip, found 3 hours ago
$188
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Nov 6 from Cincinnati to Chicago, returning Mon, Nov 10, priced at $188 found 3 hours ago
Frontier Airlines
Thu, Sep 4 - Sat, Sep 6
CVG
Cincinnati
MDW
Chicago
$190 Roundtrip, found 4 days ago
$190
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Sep 4 from Cincinnati to Chicago, returning Sat, Sep 6, priced at $190 found 4 days ago
Southwest Airlines
Sun, Aug 24 - Fri, Aug 29
CVG
Cincinnati
MDW
Chicago
$192 Roundtrip, found 1 hour ago
$192
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sun, Aug 24 from Cincinnati to Chicago, returning Fri, Aug 29, priced at $192 found 1 hour ago
Delta
Wed, Sep 10 - Fri, Sep 12
CVG
Cincinnati
MDW
Chicago
$193 Roundtrip, found 21 hours ago
$193
Roundtrip
found 21 hours ago
Select Delta flight, departing Wed, Sep 10 from Cincinnati to Chicago, returning Fri, Sep 12, priced at $193 found 21 hours ago
Southwest Airlines
Fri, Sep 12 - Sun, Sep 14
CVG
Cincinnati
MDW
Chicago
$195 Roundtrip, found 4 hours ago
$195
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Fri, Sep 12 from Cincinnati to Chicago, returning Sun, Sep 14, priced at $195 found 4 hours ago

Find the cheapest month to fly from Cincinnati (CVG) to Chicago (MDW)

October is typically the cheapest month to fly

From $118 - $328 per traveler.

Graph displaying average flight prices per month

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 $265
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $265
0
Flights from Cincinnati (CVG) to Chicago (MDW)
Origin airport
Cincinnati - Northern Kentucky Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$177
Distance
248 mi

Cincinnati to Chicago Flights

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

 

The best time to book a flight from Cincinnati to Chicago

Sunday is one of the best days to book for cheap flights from Cincinnati 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 Cincinnati 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 Cincinnati to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $89 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 Cincinnati 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 Cincinnati 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 Cincinnati - Northern Kentucky Intl. Airport (CVG) to Midway Intl. Airport (MDW) cost?
Cheap return fares from Cincinnati - Northern Kentucky Intl. Airport (CVG) to Midway Intl. Airport (MDW) start from $177. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving CVG on August 14 2025 and touching down at MDW. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from CVG to MDW?
The cheapest flights from CVG 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.
Which airlines fly direct from Cincinnati - Northern Kentucky Intl. Airport (CVG) to Midway Intl. Airport (MDW)?
When setting off from Cincinnati - Northern Kentucky Intl. Airport (CVG), you can board a nonstop flight to Midway Intl. Airport (MDW) with Southwest Airlines.
What is the cheapest airline that flies from CVG to MDW?
With fares starting at $89 for a one-way journey from CVG to MDW, Southwest Airlines is currently the cheapest carrier operating this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from CVG on September 25 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from Cincinnati - Northern Kentucky Intl. Airport (CVG) to Midway Intl. Airport (MDW)?
On average, Cincinnati - Northern Kentucky Intl. Airport (CVG) only has 1 direct flight to Midway Intl. Airport (MDW) each day. For more choices, try our easy-to-use filters. Simply enter your travel details, then click on "1 Stop" or "2+ Stops" to find flights with layovers.
What are the most popular departure times for flights from Cincinnati - Northern Kentucky Intl. Airport (CVG) to Midway Intl. Airport (MDW)?
More travelers fly between CVG and MDW at 6 AM than at any other point in the day. Rather go when it's quieter? Try choosing a quieter departure window and there's a chance you'll save on your fare as well.
What day of the week has the most flights from CVG to MDW?
If you depart on a Saturday, you'll get the greatest range of choices for flights from Cincinnati - Northern Kentucky Intl. Airport (CVG) to Midway Intl. Airport (MDW).
What is the earliest flight from Cincinnati - Northern Kentucky Intl. Airport (CVG) to Midway Intl. Airport (MDW)?
The earliest flight leaving from Cincinnati - Northern Kentucky Intl. Airport (CVG) is at around 6:50AM UTC-5. Catch this flight and you'll touch down at Midway Intl. Airport (MDW) at approximately 6:50AM UTC-6. The overall travel time is 1h.
How long does it take to fly from Cincinnati - Northern Kentucky Intl. Airport (CVG) to Midway Intl. Airport (MDW)?
It takes about 1 hour and 3 minutes to fly the 250 mi from CVG to MDW.
What airline has the least delays from CVG to MDW?
Consider booking with Southwest Airlines if you'd like to fly straight from Cincinnati - Northern Kentucky Intl. Airport (CVG) to Midway Intl. Airport (MDW) without any holdups. This airline has the best track record for punctuality, with an on-time performance of 91%. Want to be updated if anything changes? You can check your flight status using the Expedia App.
What is the best time to fly from Cincinnati - Northern Kentucky Intl. Airport (CVG) to Midway Intl. Airport (MDW)?
To touch down at Midway Intl. Airport (MDW) without delays, select a flight that takes off from Cincinnati - Northern Kentucky Intl. Airport (CVG) 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 Cincinnati - Northern Kentucky Intl. Airport (CVG)?
You can land at O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when traveling to Chicago on a direct flight from Cincinnati - Northern Kentucky Intl. Airport (CVG).
Is it cheaper to buy a plane ticket from Cincinnati - Northern Kentucky Intl. Airport (CVG) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from CVG to MDW just before your journey is typically more expensive. However, if you're flexible with your departure times and dates, you could land a cheap last-minute fare.
Is it cheaper to book a CVG to MDW flight and hotel package?
You'll typically save money by booking a CVG to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. After choosing your ideal accommodations and flights, consider adding extras such as activities, car rentals and tours.
Can I cancel or change the date of my flight from Cincinnati - Northern Kentucky Intl. Airport (CVG) to Midway Intl. Airport (MDW)?
In most instances, you can reschedule or cancel your CVG to MDW flight. However, additional charges may apply, especially if you booked over 24 hours ago. Check your itinerary for the airline's policies and fees on flight changes, or if you need further details, head to our Customer Service portal.

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*Available to One Key members.