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 | $83 (Kiwi.com) |
One-way from | $54 (Kiwi.com) |
Popular in | March |
Cheapest in | January |
Average price | $287 |
Good round-trip deal | $207 or less |
Good one-way deal | $142 or less |
Fly from
Fly to
Route
Depart
Return
Price
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Tue 1/13
8:00 am-9:03 pm
1 stop14h 03m
Chicago O'Hare Intl
Tue 1/20
5:53 pm-8:59 pm
Nonstop2h 06m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Thu 1/8
12:59 pm-9:03 pm
1 stop9h 04m
Chicago O'Hare Intl
Sun 1/11
5:53 pm-8:59 pm
Nonstop2h 06m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Thu 1/29
6:30 am-5:52 pm
1 stop12h 22m
Chicago O'Hare Intl
Sat 1/31
5:53 pm-8:59 pm
Nonstop2h 06m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Tue 3/31
7:30 am-9:10 am
Nonstop2h 40m
Chicago O'Hare Intl
Wed 4/1
5:51 pm-8:53 pm
Nonstop2h 02m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Thu 4/9
7:30 am-9:10 am
Nonstop2h 40m
Chicago O'Hare Intl
Mon 4/13
5:59 pm-8:56 am
1 stop13h 57m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Tue 4/7
8:45 pm-8:41 am
1 stop12h 56m
Chicago O'Hare Intl
Tue 4/28
9:04 am-12:04 pm
Nonstop2h 00m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Fri 5/8
12:59 pm-2:41 pm
Nonstop2h 42m
Chicago O'Hare Intl
Tue 5/12
5:15 am-7:00 pm
1 stop12h 45m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Thu 1/15
6:05 am-7:58 am
Nonstop2h 53m
Chicago O'Hare Intl
Mon 1/19
7:10 am-10:41 am
Nonstop2h 31m
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Fri 1/16
6:00 am-7:40 am
Nonstop2h 40m
Chicago Midway
Fri 1/23
5:55 pm-9:00 pm
Nonstop2h 05m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Thu 1/22
6:50 pm-8:47 pm
Nonstop2h 57m
Chicago O'Hare Intl
Sun 1/25
7:10 am-10:41 am
Nonstop2h 31m
| 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 77 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 afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from LGA to CHI are scheduled on a Sunday (77 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (22 on average).
About 15% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 160 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Saturday tends to have the lowest number of delays on this route, whereas Thursday has historically faced a higher average of delays compared to other days of the week.
Over the last year, United Airlines have had the lowest number of delays on this route, with just 12% of flights being delayed.
Entertainment
Boarding
Comfort
Crew
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Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$67 | Average$153 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$97 | Average$273 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$114 | Average$229 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$140 | Average$312 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$145 | Average$290 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$147 | Average$274 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$153 | Average$272 | FlexibilityNo cancel fee | On-time63% |