American Airlines' Main Cabin Extra provides more legroom than standard economy.
American Airlines' Flagship Business offers lie-flat seats on select transcontinental flights.
$74+ 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Jul 23 — Jul 301
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 July 18, 2025.
Popular in | December |
|---|---|
Cheapest in | September |
Average price | $260 |
Round-trip from | $147 |
One-way from | $74 |
Good round-trip deal | $194 or less |
Good one-way deal | $142 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 July 18, 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 July 18, 2025.
Sat 9/66:00 amLGA - ORD
1 stop12h 39mSpirit Airlines
Mon 9/86:30 amORD - LGA
1 stop12h 59mSpirit Airlines
Deal found 7/15$143
Wed 9/1010:30 amJFK - ORD
Nonstop2h 40mJetBlue
Wed 9/171:36 pmORD - JFK
Nonstop2h 24mJetBlue
Deal found 7/14$147
Wed 8/2711:20 amLGA - ORD
Nonstop2h 37mUnited Airlines
Wed 9/34:00 pmORD - LGA
Nonstop2h 17mUnited Airlines
Deal found 7/14$147
Tue 9/96:00 amLGA - MDW
Nonstop2h 20mSouthwest
Sat 9/136:55 amMDW - LGA
Nonstop2h 00mSouthwest
Deal found 7/15$147
Wed 9/107:30 amJFK - ORD
Nonstop2h 45mAmerican Airlines
Wed 9/171:59 pmORD - JFK
Nonstop2h 18mAmerican Airlines
Deal found 7/15$149
Sat 8/2311:00 amEWR - ORD
1 stop6h 26mSpirit Airlines
Mon 8/258:12 pmORD - EWR
1 stop12h 14mSpirit Airlines
Deal found 7/16$150
Wed 8/278:00 amEWR - ORD
Nonstop2h 38mUnited Airlines
Wed 9/36:00 amORD - EWR
Nonstop2h 15mUnited Airlines
Deal found 7/17$153
Sat 9/67:35 pmJFK - ORD
Nonstop3h 18mDelta
Mon 9/87:00 amORD - JFK
Nonstop2h 23mDelta
Deal found 7/15$157
Sat 9/610:49 amEWR - ORD
Nonstop2h 35mAmerican Airlines
Mon 9/87:12 pmORD - EWR
Nonstop2h 18mAmerican Airlines
Deal found 7/16$158
Sat 9/62:40 pmLGA - ORD
Nonstop2h 46mDelta
Mon 9/87:10 amORD - LGA
Nonstop2h 15mDelta
Deal found 7/16$158
Sat 9/139:51 amEWR - MDW
1 stop3h 37mDelta
Tue 9/166:15 pmMDW - EWR
1 stop4h 11mDelta
Deal found 7/15$167
Thu 7/3112:59 pmLGA - ORD
1 stop11h 45mMultiple Airlines
Fri 8/85:51 amORD - LGA
Nonstop2h 09mMultiple Airlines
Deal found 7/15$170
Cheapflights Fare Finder
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 July 18, 2025.
Use the filters below to find and compare flights to Chicago that are best for you.
Fly from
New York
Route
Depart
Return
Price
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Wed 9/10
8:00 am-9:55 am
Nonstop2h 55m
Chicago O'Hare Intl
Sat 9/13
7:00 am-10:22 am
Nonstop2h 22m
$147
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Wed 10/1
5:45 am-7:20 am
Nonstop2h 35m
Chicago O'Hare Intl
Wed 10/1
8:20 pm-11:34 pm
Nonstop2h 14m
$147
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Tue 9/9
6:00 am-7:20 am
Nonstop2h 20m
Chicago Midway
Sat 9/13
6:55 am-9:55 am
Nonstop2h 00m
$147
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Fri 8/1
7:55 pm-8:55 am
1 stop14h 00m
Chicago O'Hare Intl
Sat 8/9
5:51 am-9:00 am
Nonstop2h 09m
$148
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Wed 9/10
7:30 am-9:15 am
Nonstop2h 45m
Chicago O'Hare Intl
Wed 9/17
1:59 pm-5:17 pm
Nonstop2h 18m
$149
NewarkChicago
EWR - ORD
EWRORD
Newark
Sat 8/23
11:00 am-4:26 pm
1 stop6h 26m
Chicago O'Hare Intl
Wed 8/27
6:56 am-6:55 pm
1 stop10h 59m
$150
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Wed 9/3
10:30 am-12:10 pm
Nonstop2h 40m
Chicago O'Hare Intl
Wed 9/10
1:36 pm-5:00 pm
Nonstop2h 24m
$152
NewarkChicago
EWR - ORD
EWRORD
Newark
Wed 8/27
8:00 am-9:38 am
Nonstop2h 38m
Chicago O'Hare Intl
Wed 9/3
6:00 am-9:15 am
Nonstop2h 15m
$153
NewarkChicago
EWR - ORD
EWRORD
Newark
Sat 9/6
10:49 am-12:24 pm
Nonstop2h 35m
Chicago O'Hare Intl
Mon 9/8
7:12 pm-10:30 pm
Nonstop2h 18m
$158
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Tue 8/5
6:55 pm-8:49 pm
Nonstop2h 54m
Chicago O'Hare Intl
Wed 8/20
7:15 am-10:30 am
Nonstop2h 15m
$162
Showing 1-10 of 48 results
The best insider tips for flights to Chicago
Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago trip
Airlines
![American Airlines]()
American Airlines
![Alaska Airlines]()
Alaska Airlines
Alaska Airlines offers 32” legroom in Main Cabin, ideal for short domestic flights.
Saver Fare allows a carry-on, but no seat selection in advance.
![Frontier]()
Frontier
Frontier's UpFront Plus offers a guaranteed empty middle seat for extra comfort.
Frontier charges for carry-on bags; add them during booking for lower fees.
![Delta]()
Delta
Delta offers free Wi-Fi on most domestic flights for SkyMiles members.
Delta Comfort Plus provides extra legroom and early boarding on domestic flights.
![United Airlines]()
United Airlines
United's Basic Economy allows a personal item but no carry-on bags.
United Economy Plus offers extra legroom and priority boarding on domestic routes.
![Spirit Airlines]()
Spirit Airlines
Spirit's Big Front Seats offer 11 inches more legroom, ideal for comfort.
Spirit's Saver$ Club offers discounts on luggage and seats.
Airports
Our travel experts
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.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight to Chicago
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 July 11, 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 35 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 7 hours 7 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 Wednesday (189 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (72 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, JetBlue and Frontier.
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 July 18, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines to the United States. 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.
Food
7.0
Crew
8.6
Entertainment
7.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Food
7.0
Crew
8.6
Entertainment
7.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Food
7.0
Crew
8.6
Entertainment
7.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Food
7.0
Crew
8.6
Entertainment
7.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Food
7.0
Crew
8.6
Entertainment
7.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Food
7.0
Crew
8.6
Entertainment
7.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
FAQs about flying to Chicago
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsMerrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton