$59+ Cheap flights to Chicago
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Flights to Chicago in 2025
Find the latest flights to Chicago in 2025, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 2,558,603 searches and data was last updated on January 23, 2025.
Popular in | December |
|---|---|
Cheapest in | September |
Average price | $194 |
Round-trip from | $109 |
One-way from | $59 |
Good round-trip deal | $149 or less |
Good one-way deal | $108 or less |
Find flight deals to Chicago
Cheapest flights to ChicagoExplore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on January 23, 2025.
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on January 23, 2025.
Find flights to Chicago within your budget
Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 2,558,603 searches and data was last updated on January 23, 2025.
Fly from
Route
Depart
Return
Price
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Wed 2/12
10:59 am-12:37 pm
Nonstop2h 38m
Chicago O'Hare Intl
Wed 2/19
8:33 am-3:00 pm
1 stop5h 27m
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Thu 2/27
10:00 pm-11:28 am
1 stop14h 28m
Chicago Midway
Tue 3/4
8:30 am-10:00 pm
1 stop12h 30m
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Thu 4/24
6:00 am-11:26 am
1 stop6h 26m
Chicago O'Hare Intl
Tue 4/29
11:57 am-12:33 am
1 stop11h 36m
New YorkChicago
JFK - MDW
JFKMDW
New York John F Kennedy Intl
Sat 2/22
11:15 am-10:51 pm
1 stop12h 36m
Chicago Midway
Sat 3/1
4:19 pm-10:15 am
1 stop16h 56m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Thu 4/24
5:30 pm-11:11 pm
1 stop6h 41m
Chicago O'Hare Intl
Tue 4/29
11:57 am-11:03 pm
1 stop10h 06m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Sun 2/9
5:45 am-4:10 pm
1 stop11h 25m
Chicago O'Hare Intl
Wed 2/12
5:44 pm-8:29 pm
Nonstop1h 45m
NewarkChicago
EWR - ORD
EWRORD
Newark
Thu 2/20
3:03 pm-10:03 pm
1 stop8h 00m
Chicago O'Hare Intl
Mon 2/24
5:15 am-8:23 am
Nonstop2h 08m
NewarkChicago
EWR - ORD
EWRORD
Newark
Fri 3/7
6:00 am-7:44 am
Nonstop2h 44m
Chicago O'Hare Intl
Mon 3/10
8:50 am-9:09 pm
1 stop11h 19m
NewarkChicago
EWR - MDW
EWRMDW
Newark
Tue 2/11
10:00 pm-7:07 am
1 stop10h 07m
Chicago Midway
Tue 2/18
8:47 am-9:10 pm
1 stop11h 23m
NewarkChicago
EWR - ORD
EWRORD
Newark
Thu 3/6
10:09 pm-7:43 am
1 stop10h 34m
Chicago O'Hare Intl
Mon 3/10
8:50 am-9:09 pm
1 stop11h 19m
Compare providers for flights to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals to Chicago in January.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| 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*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: Out of all of the providers offering Chicago flight deals, Cheapflights users have found FlightHub to have the most accurate pricing on Cheapflights vs. their site about >95% of the time, users can find the same price on Chicago flight deals on Cheapflights and FlightHub. This is based on searches made for Chicago flights over the past month.
- Most trusted provider: FlightHub is the most trusted provider by Cheapflights users offering Chicago flight deals. With a user feedback rating of 3 out of 3 stars (3 being the best), FlightHub has received the most positive sentiment from Cheapflights users searching for flights to Chicago. This is based on data collected from Cheapflights searches made over the past month.
Best time to book a flight to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago with our price prediction graph.
Travel insights for flights to Chicago
Get recent, data-driven insights about flights to Chicago including ideal travel times, pricing trends, and more.
When is the best time to book a flight to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from New York to Chicago. Price data was last updated on January 17, 2025.
The price you pay for your flight to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 84 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
How long is the flight to Chicago?
On average, a flight from New York to Chicago takes 12 hours 17 minutes. Flights to Chicago from other popular cities in USA will vary in length. Below are a few examples of popular routes and their flight times.
When is the cheapest time to fly to Chicago?
Use this chart to determine the cheapest time to fly round-trip from New York to Chicago. Price data was last updated on December 16, 2024.
Users looking for the lowest fares to Chicago should consider flying on Tuesday mornings, when prices are typically cheapest. Budget-minded travelers will want to avoid Sunday afternoons, when prices are usually at their highest.
Weekly flight availability to Chicago
The most flights from New York to Chicago are scheduled on a Monday (179 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (53 on average).
What are the most popular airlines that fly to Chicago?
The most popular airlines flying from New York to Chicago are American Airlines, United Airlines and Spirit Airlines.
What are the cheapest airlines that fly to Chicago?
The cheapest airlines flying from New York to Chicago are Spirit Airlines, Delta and JetBlue.
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated January 23, 2025.
See what other customers who have flown with Frontier, Southwest and Delta to Chicago have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
Overall
Comfort
Entertainment
Food
Crew
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Boarding
Overall
Comfort
Entertainment
Food
Crew
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Boarding
Overall
Comfort
Entertainment
Food
Crew
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Boarding
Overall
Comfort
Entertainment
Food
Crew
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Boarding
Overall
Comfort
Entertainment
Food
Crew
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Boarding
Overall
Comfort
Entertainment
Food
Crew
Reviews
We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.