United's Economy Plus offers extra legroom, perfect for added comfort on short flights.
Prepay checked bags on United to save on fees; ideal for budget-conscious travelers.

| Most accurate provider | Justfly.com 3 stars | 
|---|---|
| Most trusted provider | Justfly.com 3 stars | 
| Round-trip from | $100 (Cheapflightsfares) | 
| One-way from | $64 (Trip.com) | 
| Popular in | June | 
| Cheapest in | January | 
| Average price | $268 | 
| Good round-trip deal | $196 or less | 
| Good one-way deal | $112 or less | 
Fly from
Fly to
Route
Depart
Return
Price
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 - 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
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
LGA - ORD
LGAORD
New York LaGuardia
Fri 11/14
8:50 pm-10:35 pm
Nonstop2h 45m
Chicago O'Hare Intl
Mon 11/17
5:50 pm-9:01 pm
Nonstop2h 11m
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Thu 12/11
6:00 am-7:30 am
Nonstop2h 30m
Chicago Midway
Wed 1/21
6:05 am-9:10 am
Nonstop2h 05m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Thu 11/13
6:00 am-9:46 am
1 stop4h 46m
Chicago O'Hare Intl
Thu 11/13
2:00 pm-5:07 pm
Nonstop2h 07m
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Wed 11/12
9:10 am-10:40 am
Nonstop2h 30m
Chicago Midway
Wed 11/12
7:15 pm-10:20 pm
Nonstop2h 05m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Thu 11/13
6:15 am-7:55 am
Nonstop2h 40m
Chicago O'Hare Intl
Mon 11/17
7:15 pm-10:35 pm
Nonstop2h 20m
| Provider | Price Accuracy | Trust Score* | 
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | 
The best time to book flights from New York LaGuardia Airport to Chicago is 72 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Currently, January is the cheapest month in which you can book a flight from New York LaGuardia Airport to Chicago (average of $86). Flying from New York LaGuardia Airport to Chicago in July is currently the most expensive (average of $155). 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 LaGuardia Airport to Chicago in the morning. By choosing this option you can save up to 35% on the cost of your flight, compared to a flight at noon.
Travelers seeking maximum savings on their New York LaGuardia Airport to Chicago flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Comfort
Boarding
Food
Overall
Entertainment
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Boarding
Food
Overall
Entertainment
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Boarding
Food
Overall
Entertainment
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Boarding
Food
Overall
Entertainment
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Boarding
Food
Overall
Entertainment
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Boarding
Food
Overall
Entertainment
Crew
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time | 
|---|---|---|---|---|
| Cheapest$66 | Average$172 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$97 | Average$273 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$114 | Average$229 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$141 | Average$313 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$147 | Average$295 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$147 | Average$273 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$156 | Average$275 | FlexibilityNo cancel fee | On-time63% |