When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 25 days in advance, which can save you up to 162% on flights from Kentucky to Chicago Midway Airport compared to booking the week you need them. Waiting 25 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $353. For sooner than that we have options available in the next 3 days from $460.
February can be a great time to fly to Chicago Midway Airport from Kentucky with a flight ticket averaging about $261. Cheapflights users have found deals in the month of February for as cheap as $157. The most expensive prices can be found in the month of January.
When flying from Kentucky to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$158 - $566
Route
Depart
Return
Price
Lexington Blue GrassChicago Midway
LEX - MDW
LEXMDW
Lexington Blue Grass
ter 6/11
1 stop3h 33m
Chicago Midway
qua 6/19
1 stop5h 14m
Louisville IntlChicago Midway
SDF - MDW
SDFMDW
Louisville Intl
sex 5/17
1 stop5h 17m
Chicago Midway
ter 5/21
1 stop4h 42m
Lexington Blue GrassChicago Midway
LEX - MDW
LEXMDW
Lexington Blue Grass
ter 5/21
1 stop7h 17m
Chicago Midway
ter 5/28
1 stop5h 09m
Louisville IntlChicago Midway
SDF - MDW
SDFMDW
Louisville Intl
sex 5/17
1 stop5h 17m
Chicago Midway
ter 5/21
2 stops8h 41m
Louisville IntlChicago Midway
SDF - MDW
SDFMDW
Louisville Intl
ter 7/16
1 stop3h 22m
Chicago Midway
qui 7/18
1 stop3h 24m
Louisville IntlChicago Midway
SDF - MDW
SDFMDW
Louisville Intl
sex 5/24
1 stop5h 55m
Chicago Midway
qua 5/29
1 stop4h 09m
Louisville IntlChicago Midway
SDF - MDW
SDFMDW
Louisville Intl
sex 5/24
1 stop5h 55m
Chicago Midway
qua 5/29
2 stops6h 17m
Lexington Blue GrassChicago Midway
LEX - MDW
LEXMDW
Lexington Blue Grass
seg 6/10
1 stop5h 51m
Chicago Midway
qua 6/19
1 stop5h 14m
Louisville IntlChicago Midway
SDF - MDW
SDFMDW
Louisville Intl
qua 5/22
3 stops33h 34m
Chicago Midway
seg 5/27
2 stops13h 40m
No data available for this route at this time. Please check back soon.
Entertainment
Comfort
Overall
Boarding
Crew
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Comfort
Overall
Boarding
Crew
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Comfort
Overall
Boarding
Crew
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Comfort
Overall
Boarding
Crew
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
1%of flight departures | Early morningMidnight to 6 am |
---|---|
29%of flight departures | Morning6 am to noon |
35%of flight departures | AfternoonNoon to 6 pm |
35%of flight departures | Evening6 pm to midnight |
Cheapflights helps you search for flights from Kentucky to Midway via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Midway from Kentucky.
Yes, we can. To see specific flights from Kentucky to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.
Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Midway from Kentucky today and book when prices fit your budget.