To save on the cost of your flight from North America to Chicago, book at least 56 days before your planned departure. Booking around this time can save you about 98% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $282 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $423.
Our data shows that February tends to be the cheapest month to fly to Chicago from North America. Users have commonly found prices around $259 for the month, but tickets can be as low as $81. Due to multiple factors, prepare for potentially higher prices in June.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from North America to Chicago as you normally would.
Fly from
Fly to
Budget
$40 - $127
Route
Depart
Return
Price
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Tue 8/27
Nonstop2h 39m
Chicago O'Hare Intl
Tue 8/27
Nonstop2h 11m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/11
Nonstop2h 54m
Chicago O'Hare Intl
Wed 6/12
Nonstop2h 29m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Tue 9/10
Nonstop2h 39m
Chicago O'Hare Intl
Sat 9/14
Nonstop2h 11m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Thu 8/22
Nonstop2h 33m
Chicago O'Hare Intl
Tue 8/27
Nonstop2h 18m
Boston Logan IntlChicago O'Hare Intl
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/11
Nonstop2h 54m
Chicago O'Hare Intl
Tue 6/18
Nonstop2h 28m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Tue 6/11
Nonstop2h 42m
Chicago O'Hare Intl
Sat 6/15
1 stop8h 08m
New York LaGuardiaChicago Midway
LGA - MDW
LGAMDW
New York LaGuardia
Tue 9/10
1 stop10h 53m
Chicago Midway
Sat 9/14
1 stop15h 00m
New York John F Kennedy IntlChicago O'Hare Intl
JFK - ORD
JFKORD
New York John F Kennedy Intl
Sat 8/24
Nonstop2h 45m
Chicago O'Hare Intl
Wed 8/28
Nonstop2h 19m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Sat 8/17
Nonstop2h 59m
Chicago O'Hare Intl
Wed 8/21
Nonstop2h 14m
No data available for this route at this time. Please check back soon.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
11%of flight departures | Early morningMidnight to 6 am |
---|---|
37%of flight departures | Morning6 am to noon |
37%of flight departures | AfternoonNoon to 6 pm |
15%of flight departures | Evening6 pm to midnight |
Cheapflights makes it easy to find North America to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from North America to Chicago for you. Better yet — we are completely free to use.
Certainly. Search results for flights to Chicago from North America shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Yes! Start tracking prices for North America to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.