
| Round-trip from | $100 (Cheapflightsfares) | 
|---|---|
| One-way from | $64 (Trip.com) | 
| Popular in | December | 
| Cheapest in | September | 
| Average price | $384 | 
Fly from
Fly to
Route
Depart
Return
Price
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Thu 11/20
1:00 pm-12:13 am
1 stop12h 13m
Chicago Midway
Thu 12/4
2:16 pm-12:07 am
1 stop8h 51m
NewarkChicago
EWR - MDW
EWRMDW
Newark
Thu 12/4
10:30 pm-10:12 pm
1 stop24h 42m
Chicago Midway
Sun 12/7
7:44 am-10:45 am
Nonstop2h 01m
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Wed 11/19
10:50 am-12:39 pm
Nonstop2h 49m
Chicago O'Hare Intl
Wed 11/19
6:33 pm-10:05 pm
Nonstop2h 32m
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Sat 11/15
8:35 am-10:00 am
Nonstop2h 25m
Chicago Midway
Mon 11/17
7:15 pm-10:20 pm
Nonstop2h 05m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Sat 11/15
11:30 am-1:17 pm
Nonstop2h 47m
Chicago O'Hare Intl
Mon 11/17
9:30 am-12:41 pm
Nonstop2h 11m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Thu 11/13
6:15 am-7:55 am
Nonstop2h 40m
Chicago O'Hare Intl
Wed 11/19
7:00 am-10:15 am
Nonstop2h 15m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Tue 11/11
10:59 am-12:27 am
1 stop14h 28m
Chicago O'Hare Intl
Wed 11/12
10:52 am-11:21 pm
1 stop11h 29m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Thu 1/15
7:30 am-9:27 am
Nonstop2h 57m
Chicago O'Hare Intl
Sun 1/18
10:45 am-1:58 pm
Nonstop2h 13m
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Sat 2/7
7:00 pm-8:53 pm
Nonstop2h 53m
Chicago O'Hare Intl
Sat 2/14
7:30 am-10:56 am
Nonstop2h 26m
NewarkChicago
EWR - MDW
EWRMDW
Newark
Sun 11/23
10:13 am-11:42 am
Nonstop2h 29m
Chicago Midway
Tue 12/2
2:49 pm-1:10 am
1 stop9h 21m
Currently, April is the cheapest month in which you can book a flight from Connecticut to Indiana (average of $181). Flying from Connecticut to Indiana in March is currently the most expensive (average of $270). 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 Connecticut to Indiana in the evening. By choosing this option you can save up to 29% on the cost of your flight, compared to a flight at noon.
Travelers seeking maximum savings on their Connecticut to Indiana flight should consider departing on Saturday at noon when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Food
Crew
Comfort
Overall
Boarding
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Food
Crew
Comfort
Overall
Boarding
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Food
Crew
Comfort
Overall
Boarding
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Food
Crew
Comfort
Overall
Boarding
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Food
Crew
Comfort
Overall
Boarding
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time | 
|---|---|---|---|---|
| Cheapest$239 | Average$387 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$239 | Average$391 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$248 | Average$386 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$269 | Average$370 | FlexibilityNo cancel fee | On-time63% |