
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $101 (Mytrip) |
One-way from | $50 (Booking.com) |
Popular in | December |
Cheapest in | August |
Average price | $421 |
Good round-trip deal | $276 or less |
Good one-way deal | $184 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoOwensboro
ORD - OWB
ORDOWB
Chicago O'Hare Intl
Di 4/21
11:20 am-12:55 pm
Nonstop1h 35m
Owensboro Daviess County
Mi 4/22
9:00 am-10:40 am
Nonstop1h 40m
ChicagoOwensboro
ORD - OWB
ORDOWB
Chicago O'Hare Intl
Di 4/7
11:20 am-12:55 pm
Nonstop1h 35m
Owensboro Daviess County
Mi 4/8
9:00 am-10:40 am
Nonstop1h 40m
ChicagoOwensboro
ORD - OWB
ORDOWB
Chicago O'Hare Intl
Sa 5/23
11:20 am-12:55 pm
Nonstop1h 35m
Owensboro Daviess County
Di 5/26
2:35 pm-4:15 pm
Nonstop1h 40m
ChicagoOwensboro
ORD - OWB
ORDOWB
Chicago O'Hare Intl
So 5/3
11:20 am-12:55 pm
Nonstop1h 35m
Owensboro Daviess County
Di 5/5
2:35 pm-4:15 pm
Nonstop1h 40m
ChicagoLouisville
ORD - SDF
ORDSDF
Chicago O'Hare Intl
Mi 4/22
8:15 am-2:31 pm
1 stop5h 16m
Louisville Intl
Di 4/28
7:56 am-12:45 pm
1 stop5h 49m
ChicagoIndianapolis
MDW - IND
MDWIND
Chicago Midway
Mi 4/29
2:10 pm-9:25 pm
1 stop6h 15m
Indianapolis
Di 5/5
5:10 pm-5:10 pm
Nonstop1h 00m
ChicagoOwensboro
ORD - OWB
ORDOWB
Chicago O'Hare Intl
Sa 4/4
4:51 pm-6:50 pm
2 stops25h 59m
Owensboro Daviess County
Di 4/7
2:35 pm-4:15 pm
Nonstop1h 40m
ChicagoLouisville
MDW - SDF
MDWSDF
Chicago Midway
Mo 5/18
7:45 am-9:55 am
Nonstop1h 10m
Louisville Intl
Di 5/19
1:35 pm-8:10 pm
2 stops7h 35m
ChicagoOwensboro
ORD - OWB
ORDOWB
Chicago O'Hare Intl
Do 4/9
5:25 am-6:50 pm
2 stops13h 25m
Owensboro Daviess County
Di 4/14
2:35 pm-4:15 pm
Nonstop1h 40m
ChicagoLouisville
ORD - SDF
ORDSDF
Chicago O'Hare Intl
Sa 5/2
1:29 pm-11:59 pm
2 stops9h 30m
Louisville Intl
Di 5/5
7:56 am-12:45 pm
1 stop5h 49m
Currently, April is the cheapest month in which you can book a flight from Chicago to Indiana (average of $141). Flying from Chicago to Indiana in January is currently the most expensive (average of $291). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
It’s optimal to fly from Chicago to Indiana at noon. By choosing this option you can save up to 28% on the cost of your flight, compared to a flight in the evening.
Travelers seeking maximum savings on their Chicago to Indiana flight should consider departing on Friday mornings when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to USIN are scheduled on a Monday (66 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (13 on average).
Overall
Comfort
Crew
Food
Entertainment
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Comfort
Crew
Food
Entertainment
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Comfort
Crew
Food
Entertainment
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Overall
Comfort
Crew
Food
Entertainment
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$333 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$191 | Average$376 | FlexibilityNo cancel fee | On-time71% |