
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $191 (Cheapflightsfares) |
One-way from | $95 (Trip.com) |
Popular in | June |
Cheapest in | January |
Average price | $326 |
Good round-trip deal | $202 or less |
Good one-way deal | $150 or less |
Fly from
Fly to
Route
Depart
Return
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Fri 9/25
7:25 am-8:45 am
Nonstop2h 20m
Chicago Midway
Mon 9/28
5:00 am-8:00 am
Nonstop2h 00m
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Thu 8/13
6:00 am-7:15 am
Nonstop2h 15m
Chicago Midway
Sun 8/16
5:25 am-8:25 am
Nonstop2h 00m
NewarkChicago
EWR - ORD
EWRORD
Newark
Tue 9/22
3:20 pm-8:55 pm
1 stop6h 35m
Chicago O'Hare Intl
Thu 9/24
1:50 pm-10:24 pm
1 stop7h 34m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Thu 9/24
7:20 am-9:00 am
Nonstop2h 40m
Chicago O'Hare Intl
Mon 9/28
6:00 am-9:15 am
Nonstop2h 15m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Thu 8/20
4:00 pm-6:03 pm
Nonstop3h 03m
Chicago O'Hare Intl
Mon 8/24
7:05 pm-10:34 pm
Nonstop2h 29m
NewarkChicago
EWR - ORD
EWRORD
Newark
Wed 7/15
8:19 pm-10:06 pm
Nonstop2h 47m
Chicago O'Hare Intl
Fri 7/17
9:30 pm-12:53 am
Nonstop2h 23m
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Wed 7/22
8:55 am-3:55 pm
1 stop8h 00m
Chicago Midway
Tue 7/28
5:15 am-8:15 am
Nonstop2h 00m
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Sat 9/26
5:50 pm-7:15 pm
Nonstop2h 25m
Chicago Midway
Sat 10/3
2:20 pm-9:20 pm
1 stop6h 00m
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Sat 8/15
5:50 pm-7:15 pm
Nonstop2h 25m
Chicago Midway
Mon 8/17
7:50 pm-10:55 pm
Nonstop2h 05m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Tue 7/14
5:25 pm-7:12 pm
Nonstop2h 47m
Chicago O'Hare Intl
Sat 7/18
7:45 pm-11:15 pm
Nonstop2h 30m
Currently, January is the cheapest month in which you can book a flight from New York to Illinois (average of $199). Flying from New York to Illinois in June is currently the most expensive (average of $352). 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 New York to Illinois in the evening. By choosing this option you can save up to 22% on the cost of your flight, compared to a flight in the afternoon.
The most flights from NYC to USIL are scheduled on a Monday (192 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (93 on average).
Booking 82 days in advance of your planned departure date is, on average, the best time to get cheap flights from New York to Illinois. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Travelers seeking maximum savings on their New York to Illinois flight should consider departing on Wednesday evenings when fares are most often at their lowest. Thursday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Comfort
Boarding
Crew
Entertainment
Food
Overall
Reviews
Reza,Jun 2026
TPA - MDW
Comfort
Boarding
Crew
Entertainment
Food
Overall
Reviews
Reza,Jun 2026
TPA - MDW
Comfort
Boarding
Crew
Entertainment
Food
Overall
Reviews
Reza,Jun 2026
TPA - MDW
Comfort
Boarding
Crew
Entertainment
Food
Overall
Reviews
Reza,Jun 2026
TPA - MDW
Comfort
Boarding
Crew
Entertainment
Food
Overall
Reviews
Reza,Jun 2026
TPA - MDW
Comfort
Boarding
Crew
Entertainment
Food
Overall
Reviews
Reza,Jun 2026
TPA - MDW
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$39 | Average$171 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$74 | Average$326 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$98 | Average$246 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$147 | Average$401 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$418 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$164 | Average$315 | FlexibilityNo cancel fee | On-time63% |