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Cheap flights from Cincinnati to Chicago from $55

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Cincinnati to Chicago departing on 12/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

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Southwest Logo
5:35 am - 1:50 pmCVG-MDW
9h 15m1 stop
Southwest Logo
1:35 pm - 11:05 pmMDW-CVG
8h 30m2 stops
$237Southwest
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Thu, Feb 12 - Tue, Feb 17
Southwest Logo
7:00 am - 7:15 amCVG-MDW
1h 15mnonstop
Southwest Logo
2:30 pm - 10:30 pmMDW-CVG
7h 00m2 stops
$238Southwest
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Sat, Dec 13 - Mon, Dec 15
Frontier Logo
8:20 pm - 12:53 pmCVG-MDW
41h 33m2 stops
Frontier Logo
9:43 am - 8:24 pmMDW-CVG
9h 41m1 stop
$239Frontier
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Sun, Jan 4 - Fri, Jan 16
Southwest Logo
5:50 am - 10:10 amCVG-MDW
5h 20m1 stop
Southwest Logo
2:30 pm - 10:30 pmMDW-CVG
7h 00m2 stops
$240Southwest
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Thu, Dec 11 - Mon, Dec 15
Southwest Logo
6:35 am - 6:50 amCVG-MDW
1h 15mnonstop
Southwest Logo
5:30 pm - 7:40 pmMDW-CVG
1h 10mnonstop
$242Southwest
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Mon, Jan 5 - Wed, Jan 7
Delta Logo
8:40 am - 11:55 amCVG-MDW
4h 15m1 stop
Delta Logo
5:13 pm - 12:04 amMDW-CVG
5h 51m1 stop
$243Delta
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Tue, Dec 9 - Thu, Dec 11
Southwest Logo
6:35 am - 6:50 amCVG-MDW
1h 15mnonstop
Southwest Logo
12:25 pm - 6:15 pmMDW-CVG
4h 50m1 stop
$244Southwest
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Thu, Dec 18 - Thu, Dec 25
Southwest Logo
7:00 am - 7:15 amCVG-MDW
1h 15mnonstop
Southwest Logo
6:20 pm - 8:35 pmMDW-CVG
1h 15mnonstop
$245Southwest
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Thu, Dec 11 - Mon, Dec 15
Delta Logo
6:00 am - 12:34 pmCVG-MDW
7h 34m2 stops
Delta Logo
5:13 pm - 12:04 amMDW-CVG
5h 51m1 stop
$248Delta
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Tue, Dec 9 - Thu, Dec 11
Southwest Logo
7:00 am - 7:15 amCVG-MDW
1h 15mnonstop
Southwest Logo
5:35 am - 12:25 pmMDW-CVG
5h 50m1 stop
$249Southwest
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Tue, Dec 16 - Tue, Dec 23

Southwest flights from Cincinnati to Chicago Midway Airport

Our best Southwest deals on Cincinnati to Chicago Midway Airport flight tickets
Southwest
Feb 12
CVG5:35 amCincinnati Cinci./N. Kentucky
9h 15m
1 stop
MDW1:50 pmChicago Midway
Feb 17
MDW1:35 pmChicago Midway
8h 30m
2 stops
CVG11:05 pmCincinnati Cinci./N. Kentucky
$237
Find similar
Southwest
Dec 13
CVG7:00 amCincinnati Cinci./N. Kentucky
1h 15m
MDW7:15 amChicago Midway
Dec 15
MDW2:30 pmChicago Midway
7h 00m
2 stops
CVG10:30 pmCincinnati Cinci./N. Kentucky
$238
Find similar
Southwest
Nov 24
CVG6:35 amCincinnati Cinci./N. Kentucky
1h 15m
MDW6:50 amChicago Midway
Nov 28
MDW7:35 pmChicago Midway
1h 10m
CVG9:45 pmCincinnati Cinci./N. Kentucky
$239
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Frontier flights from Cincinnati to Chicago Midway Airport

Our best Frontier deals on Cincinnati to Chicago Midway Airport flight tickets
Frontier
Jan 4
CVG8:20 pmCincinnati Cinci./N. Kentucky
41h 33m
2 stops
MDW12:53 pmChicago Midway
Jan 16
MDW9:43 amChicago Midway
9h 41m
1 stop
CVG8:24 pmCincinnati Cinci./N. Kentucky
$239
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Frontier
Dec 5
CVG12:02 pmCincinnati Cinci./N. Kentucky
11h 10m
1 stop
MDW10:12 pmChicago Midway
Dec 7
MDW6:37 pmChicago Midway
15h 15m
1 stop
CVG10:52 amCincinnati Cinci./N. Kentucky
$253
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Frontier
Dec 6
CVG11:57 amCincinnati Cinci./N. Kentucky
24h 11m
2 stops
MDW11:08 amChicago Midway
Dec 7
MDW7:27 pmChicago Midway
14h 16m
1 stop
CVG10:43 amCincinnati Cinci./N. Kentucky
$262
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momondo Fare Finder

 
Customize your flight search to find flights from Cincinnati to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 20, 2025.
Use the filters below to find and compare flights from Cincinnati to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 2/12

5:35 am-1:50 pm

1 stop9h 15m

Chicago Midway

Tue 2/17

1:35 pm-11:05 pm

2 stops8h 30m

$237

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 12/13

7:00 am-7:15 am

Nonstop1h 15m

Chicago Midway

Mon 12/15

2:30 pm-10:30 pm

2 stops7h 00m

$238

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sun 1/4

8:20 pm-12:53 pm

2 stops41h 33m

Chicago Midway

Fri 1/16

9:43 am-8:24 pm

1 stop9h 41m

$239

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 12/11

5:50 am-10:10 am

1 stop5h 20m

Chicago Midway

Mon 12/15

2:30 pm-10:30 pm

2 stops7h 00m

$240

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Mon 1/5

6:35 am-6:50 am

Nonstop1h 15m

Chicago Midway

Wed 1/7

5:30 pm-7:40 pm

Nonstop1h 10m

$242

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 12/9

8:40 am-11:55 am

1 stop4h 15m

Chicago Midway

Thu 12/11

5:13 pm-12:04 am

1 stop5h 51m

$243

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 12/18

6:35 am-6:50 am

Nonstop1h 15m

Chicago Midway

Thu 12/25

12:25 pm-6:15 pm

1 stop4h 50m

$244

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 12/11

7:00 am-7:15 am

Nonstop1h 15m

Chicago Midway

Mon 12/15

6:20 pm-8:35 pm

Nonstop1h 15m

$245

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 12/9

6:00 am-12:34 pm

2 stops7h 34m

Chicago Midway

Thu 12/11

5:13 pm-12:04 am

1 stop5h 51m

$248

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 12/16

7:00 am-7:15 am

Nonstop1h 15m

Chicago Midway

Tue 12/23

5:35 am-12:25 pm

1 stop5h 50m

$249

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Cincinnati to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Cincinnati. The lowest ticket price found for a Tuesday departure recently was $380. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Cincinnati because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $436.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Cincinnati in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $356 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $446. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Cincinnati Cinci./N. Kentucky to Chicago Midway flight route?

Fly from Cincinnati Cinci./N. Kentucky to Chicago Midway for the best Cincinnati Cinci./N. Kentucky - Chicago Midway flight prices

What cabin class options are available on Cincinnati Cinci./N. Kentucky to Chicago Midway flights?

There is only 1 cabin class available to choose from on Cincinnati Cinci./N. Kentucky to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Cincinnati to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Cincinnati to Chicago Midway Airport.

When to book flights from Cincinnati to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Cincinnati to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Cincinnati to Chicago Midway Airport (CVG to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cincinnati to Chicago Midway Airport

Best Price Found

$154

Fastest flight time

1h 05m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Cincinnati in the past 72 hours is $154. The best round-trip flight deal from Cincinnati to Chicago Midway Airport found on momondo in the last 72 hours is $341.
The fastest flight from Cincinnati to Chicago Midway Airport takes 1h 05m
Direct flights go from Cincinnati to Chicago Midway Airport every day.
Search flight deals

  • How far is Cincinnati Cinci./N. Kentucky to Chicago Midway by plane?

    Chicago Midway is 251.4 mi away from Cincinnati Cinci./N. Kentucky. A reasonable flight in good conditions will take 1h 15m.

  • When did momondo last update prices for flights from Cincinnati Cinci./N. Kentucky Airport to Chicago Midway Airport?

    Prices for flights from Cincinnati Cinci./N. Kentucky Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Cincinnati Cinci./N. Kentucky Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Cincinnati Cinci./N. Kentucky Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Cincinnati Cinci./N. Kentucky Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Cincinnati to Chicago Midway Airport?

  • What is the most popular airline from Cincinnati to Chicago Midway Airport?

Best airlines flying from Cincinnati to Chicago Midway Airport

Compare and see reviews for airlines that fly from Cincinnati to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $183Free CancellationRating
8.0
4,251 reviews
Search Southwest flights

  • Southwest Flights From Cincinnati to Chicago Midway Airport

    Across 2 Southwest flights from Cincinnati to Chicago Midway Airport this week, the average price was $311, with the best Southwest deals starting from $183 round-trip. 4,251 users have rated Southwest on momondo, with an average score of 8.0/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Cincinnati to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Cincinnati.

Can I find flights from Cincinnati to Chicago with flexible booking policies on momondo?

All flight searches from Cincinnati to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Cincinnati to Chicago?

momondo helps you find the best flight between Cincinnati and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Cincinnati to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Cincinnati are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway Airport trip

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