$97 Find Cheap Flights to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 7/21. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$192
Typical prices: $211-$373
JetBlue
Sat 8/1Sat 8/8
JFK - ORD • Non-stop
Cheapest one-way
$97
Typical prices: $142-$267
JetBlue
Tue 7/21
JFK - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts and KAYAK users. AI can make mistakes.
Frontier's Economy Bundle adds carry-on and seat selection to avoid extra fees.
American Basic Economy boards late; United Economy Plus adds 6 inches of legroom.
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Top routes
Cheapest
Most popular
Insights
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When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 32% compared to booking last minute.
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When to travel
Cheapest • 13% price drop
Most popular
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Flight Deals
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Flight Deals

Cheap Flights to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Chicago

Sat, Aug 1 - Sat, Aug 8
JetBlue Logo
7:10 pm - 9:11 pm
JFK
-
ORD
3h 01mnonstop
JetBlue Logo
5:27 pm - 9:00 pm
ORD
-
JFK
2h 33mnonstop
$192JetBlue
Wed, Aug 26 - Sun, Aug 30
American Airlines Logo
8:29 pm - 10:30 pm
LGA
-
ORD
3h 01mnonstop
American Airlines Logo
6:00 am - 9:13 am
ORD
-
LGA
2h 13mnonstop
$192American Airlines
Wed, Jul 22 - Wed, Aug 5
United Airlines Logo
6:10 am - 7:49 am
LGA
-
ORD
2h 39mnonstop
United Airlines Logo
3:00 pm - 6:22 pm
ORD
-
LGA
2h 22mnonstop
$194United Airlines
Thu, Aug 20 - Tue, Aug 25
Delta Logo
4:00 pm - 6:03 pm
LGA
-
ORD
3h 03mnonstop
Delta Logo
6:00 am - 9:09 am
ORD
-
LGA
2h 09mnonstop
$195Delta
Tue, Aug 4 - Tue, Aug 11
Frontier Logo
1:25 pm - 4:08 pm
DFW
-
ORD
2h 43mnonstop
Frontier Logo
6:19 am - 4:07 pm
ORD
-
DFW
9h 48m
1 stop
$196Frontier
Thu, Aug 20 - Sun, Aug 23
Frontier Logo
6:07 pm - 8:31 pm
DFW
-
MDW
2h 24mnonstop
Frontier Logo
9:26 pm - 11:59 pm
MDW
-
DFW
2h 33mnonstop
$196Frontier
Tue, Jul 28 - Tue, Aug 4
Delta Logo
8:45 pm - 10:36 pm
LGA
-
ORD
2h 51mnonstop
Delta Logo
8:12 pm - 11:44 pm
ORD
-
LGA
2h 32mnonstop
$196Delta
Fri, Sep 11 - Sun, Sep 13
United Airlines Logo
7:14 pm - 9:00 pm
EWR
-
ORD
2h 46mnonstop
United Airlines Logo
5:00 am - 8:14 am
ORD
-
EWR
2h 14mnonstop
$207United Airlines
Tue, Jul 28 - Sat, Aug 1
Multiple Airlines Logo
2:25 pm - 7:15 pm
DCA
-
ORD
5h 50m
1 stop
Multiple Airlines Logo
9:57 pm - 12:51 pm
ORD
-
DCA
13h 54m
1 stop
$245Multiple Airlines
Mon, Aug 10 - Thu, Aug 13
Multiple Airlines Logo
8:33 pm - 8:02 am
IAD
-
ORD
12h 29m
1 stop
Multiple Airlines Logo
5:13 pm - 11:20 am
ORD
-
IAD
17h 07m
2 stops
$248Multiple Airlines
Booking Insights

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Chicago?

These are the best round-trip prices found by users searching on KAYAK in the last 5 days.

In the last 5 days, the cheapest flight deal to Chicago was found on the route from New York, at $192 return. The most popular connection is from Los Angeles to Chicago and KAYAK users have found round-trip deals for as low as $231 in the last 5 days.

How much is a flight to Chicago?

The average and cheapest price for all round-trip flights to Chicago from each origin found by users searching on KAYAK in the last month.

A flight to Chicago costs $385 on average. The cheapest price found on KAYAK in the last 2 weeks cost $29 and departed from Nashville. The most popular routes on KAYAK are New York to Chicago which costs $346 on average, and Boston to Chicago, which costs $328 on average.

See prices from:

What is the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Chicago is Friday where round-trip tickets can be as cheap as $391. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $580 on average.

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights to Chicago is January, where tickets cost $259 on average for return flights. On the other hand, the most expensive months are June and May, where the average cost of tickets from the United States is $377 and $334 respectively. For one-way flights, the best month to travel is October with an average price of $163.

What is the cheapest time of day to fly to Chicago?

The average price for all round-trip flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Chicago is generally at night, when round-trip flights cost $303 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $372.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From Dallas/Fort Worth Airport $245 round-trip, from Fayetteville $331 round-trip, from Jacksonville $348 round-trip.

How far in advance should I book a flight to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price, you should book around 2 weeks before departure, which saves you about 32% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport (RFD), with an average flight price of $128.

Expert advice

Expert advice for your flight to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, Frontier, Delta, ORD and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines and Alaska Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Good to know - Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flight$97
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from New York John F Kennedy Airport to Chicago O'Hare Airport

When to book flights to Chicago

Are your dates flexible? Find out the best times to travel to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. The information is for flights to Chicago based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

Flights to Chicago: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew to Chicago 
JoanneFlew with United Airlines
DEN
-
ORD
Jun 2026
The runway to gate took a bit of time. So if you have a short layover pay for a seat up front .
CupcakeFlew with Alaska Airlines
SAN
-
ORD
Apr 2026
Please bring a water bottle for hydration during the flight.
Verified travelerFlew with American Airlines
RSW
-
ORD
May 2026
Don’t plan on using overhead bin space if you board after group 4 on any American flights using 737’s. They are frequently full by the time the 4th group boards. And, if your carry on bag has to be checked at the gate, be sure it has nothing breakable inside, as it may not survive that process.
Verified travelerFlew with American Airlines
GSP
-
ORD
Apr 2026
Chicago has a enormous airport so be ready to walk and transfer to international flights by train via terminal
Dr. JosephFlew with United Airlines
ATL
-
ORD
Apr 2026
Always keep track of the weather at both locations and where the inbound flight is coming from.
Verified travelerFlew with American Airlines
SGF
-
ORD
May 2026
Arrive airport early, esp if checking bags - std procedure but vital here
Verified travelerFlew with United Airlines
ATL
-
ORD
Apr 2026
Make sure the flight you select has more than 3 hours as time allotted for transiting to another flight. Most of United Airlines flights get delayed and if you don’t have enough time, you’ll be missing the next flight for sure. Have extra budget for shelter expenses because most of the economy tickets does not qualify for shelter accommodation/ voucher when your flight is delayed.
YesicaFlew with United Airlines
CHS
-
ORD
Feb 2026
Utilize the mobile app of your airline it will give you all the updates and information you need
BillFlew with Frontier
MCO
-
ORD
Dec 2025
Wear comfortable clothing and make sure you layer. We went from 80o to 30o,
Thrinadh KumarFlew with United Airlines
OGG
-
ORD
Dec 2025
Flight is conjusted. Difficult to sleep. Carry pillows and sleep well beforeyou travel
StephenFlew with United Airlines
SMF
-
ORD
Jan 2026
If you're trying to make a connecting flight make sure you allow PLENTY of time between flights or be prepared to miss the next flight. Make sure to use the restroom at the last possible moment before landing because you could be sitting on the taxiway for 5 more minutes... 5 more minutes... 5 more minutes... until it's been nearly 2 hours. Don't trust the airline provided ETA provided by apps they don't update it until long after you're delayed. If someone is showing up to give you a ride, make sure they have hours to wait for you.
JeremyFlew with United Airlines
XNA
-
ORD
Nov 2025
Beware short connection times on flights connecting in Chicago.
DouglasFlew with American Airlines
HSV
-
ORD
Jun 2025
Check your app for delay notices. This notice did come out early in the morning - I failed to check it. Checking it could have saved 4 hours at the airport
Verified travelerFlew with British Airways
DSM
-
ORD
Jun 2025
Make sure your luggage receipts have the ID numbers on them
StaceyFlew with American Airlines
PHX
-
ORD
Feb 2025
Don’t be that person who holds up the plane because of your carry on. Whether putting in over bin (able to lift it on your own) or refusing to not listen when space is full and need to check it.
StephenFlew with United Airlines
EWR
-
ORD
Jan 2025
Don't bring a carry on roller bag. It won't fit. They will gate check it. It will take forever.
RodFlew with United Airlines
SAN
-
ORD
Sep 2024
Yes! Don’t reserve a flight with less than 1 1/2 hour connection time or you have a good possibility of missing your connection.
FrancisFlew with United Airlines
LAX
-
ORD
Sep 2024
Check the weather, or bring a. Raincoat! Being from sunny California, I forget it isn’t always sunshine in other states!
GeraldFlew with Alaska Airlines
SFO
-
ORD
Oct 2024
Book a flight as early in the day as possible to avoid incoming flight delays.
AdamFlew with Southwest
DEN
-
ORD
Oct 2024
Arriving T5 at ORD on Southwest is often a LONG walk, with no moving walkways going out, to baggage claim / pickup.
DinaFlew with United Airlines
HSV
-
ORD
Nov 2024
Be prepared for delays and plan to check your luggage. Overhead bins are ⅓ the size of a typical bin.
KimFlew with American Airlines
SNA
-
ORD
Nov 2024
Bring extra foods and buy extra drinks bring your meds
LeoFlew with United Airlines
CLT
-
ORD
Jun 2024
Get precheck TSA if you’re flying in early morning. Get a seat on the right side of the plane if you want to see sunrise.
Verified travelerFlew with American Airlines
PHL
-
ORD
Jul 2024
Fly out the night before you have anything to do in Chicago so you don’t get delayed and miss out on plans
CameonFlew with Frontier
SLC
-
ORD
Jul 2024
Fly Delta! Book directly through the airline, not a second booking party.
GailFlew with JetBlue
BOS
-
ORD
Jul 2024
Prepare for a long wait after you actually touch down. Ohare Airport is HUGE and you can taxi for a long time.
MichelleFlew with United Airlines
MBS
-
ORD
Apr 2024
Bring water on board and charge your devices in advance.
Verified travelerFlew with Southwest
LAS
-
ORD
May 2024
Leave plenty of time to get your bag in Chicago if you check one. Took 45 minutes to get my bag this time.
Verified travelerFlew with Alaska Airlines
SDF
-
ORD
Apr 2024
If flight gets delayed. Be sure to ask the airlines you traveled with, to rebook the next available flight immediately.
KariFlew with British Airways
LSE
-
ORD
May 2024
Ask for assistance. Chicago is huge airport 🛫 and can get lost easy.
CindyFlew with Southwest
TPA
-
MDW
Mar 2024
Don’t check a bag. Chicago takes forever to get your baggage.
yvgeniFlew with United Airlines
EWR
-
ORD
Jan 2024
Check the weather before flying , and don’t rely on getting on time to your destination

FAQs - booking Chicago flights

  • Which Chicago airport is closest to downtown?

    Chicago Midway International Airport (MDW) is certainly your choice if you are looking for quick (roughly 20 minutes) and convenient public transport access to the downtown area. However, if you are renting a car, then Chicago O'Hare International Airport (ORD) is also only about a 20-minute drive away from downtown.

  • How to get to the Loop from Chicago’s airports?

    If you are coming from Chicago O'Hare International Airport (ORD) and plan on taking public transport to get to the Loop, then the best option is to simply get on the Blue Line and head towards Forest Park, get off at Jackson and you’ll have arrived at the Loop. The trip will take about 40 minutes (19 stops) and will cost around $5. From Chicago Midway International Airport (MDW) to the Loop, you simply hop on the Orange Line at Midway and ride the train to its terminus at the Loop. It will take around 20 minutes and will cost approximately $3.

  • What to do in Chicago O'Hare International Airport (ORD)?

    Chicago O'Hare International Airport (ORD) offers one of the only aeroponic airport gardens in the world. Ticketed customers are able to visit the wonderful garden where they can relax or enjoy a meal. The garden is located in Terminal 3’s O’Hare Rotunda Building.

  • How far are the Chicago airports from each other?

    If you are driving a personal vehicle, Chicago O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are around an hour drive away from each other. Possibly the most economical way to get between the two is to take the CTA which will require one transfer downtown and will take around an hour and a half while costing approximately $5. There is also the option of a shuttle bus, which will take about an hour and will cost around $25 for a one-way ticket.

  • What is the best way to get from the airport to downtown Chicago?

    If you are landing at Chicago O'Hare International Airport (ORD) and you are taking public transport, there is an easy way to get to the downtown area. You can take the train, or the L. The Blue Line serves the route between the airport and downtown Chicago 24/7. If you are landing at Chicago Midway International Airport (MDW), you can also take the L, but this airport is served by the Orange Line. There are also 9 CTA buses that serve MDW if the Orange Line is not your preferred mode of transportation.

  • Do Chicago’s airports offer assistance for passengers with limited mobility?

    Of course, both Chicago O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) offer services for travelers with limited mobility. Along with wheelchair service and accessible facilities, you can also arrange to have assistance navigating the airport after you land in Chicago. Contact your airline in advance to book these services and let them know how best to assist you.

  • Are there any direct flights to Chicago from other major U.S. airports?

    Yes, there are plenty of direct flights to Chicago from many other major destinations in the United States. Chicago O'Hare International Airport (ORD) especially is a major transit destination, so direct flights to this airport are quite frequent. You will find direct flights to O’Hare from places like Cincinnati, Los Angeles, all three of the airports in New York City, and more.

  • Are there any hotels located in or near either of the Chicago airports?

    Yes, both Chicago O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) have several airports close by. The Hilton Chicago O’Hare Airport Hotel is directly across from ORD’s terminal building. There are also several other hotels nearby that offer free shuttle service. The closest hotel to MDW is the Hyatt Place Chicago Midway Airport.

  • What is the cheapest flight to Chicago?

    In the last 5 days, the cheapest flight deal to Chicago was found on the route from New York, at $192 return. The most popular connection is from Los Angeles to Chicago and KAYAK users have found round-trip deals for as low as $231 in the last 5 days.

  • Which Chicago airport is closest to central Chicago?

    Out of the 3 airports in Chicago, Chicago Midway Airport is the nearest to the city center (9 miles). You'll travel 16 miles to reach the center of Chicago if you land in Chicago O'Hare Airport and 79 miles if you land in Chicago Greater Rockford.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $385. The cheapest price found on KAYAK in the last 2 weeks cost $29 and departed from Nashville Intl Airport.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $246 or less one-way and $377 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.
  • Public transit in Chicago conveniently links up directly with both O’Hare International Airport (ORD) and Chicago Midway International Airport (MDW). For O’Hare, the CTA Blue Line is located right within the airport and will get you to downtown Chicago in around 40 minutes while costing you about $5. At Chicago Midway International Airport (MDW), the CTA Orange Line can be found within the airport and will take around 20 minutes to get you downtown and will cost around $3.
  • If you are traveling with pets, you will be happy to know that both O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) offer animal relief areas in the terminals. At O'Hare International Airport (ORD), Service Animal Relief Areas (SARA) are located on the outside security on the lower levels of Terminals 1, 2 and 5 and inside security in the Terminal 3 Rotunda and Main Hall. At Chicago Midway International Airport (MDW), these areas are at gate A-5 and outside door #4 of baggage claim.
  • The Family Lounge at O'Hare International Airport (ORD) is an educational and excitement-filled place for kids and parents to relax and have a bit of a fun before or after their flight. There is live entertainment at various times throughout the year, especially during the holiday season, featuring musicians, caricature artists and more. This is located in Terminal 2, just beyond security.
  • If you need to refresh yourself after your flight to Chicago, you can use the shower facilities at the Hilton Health Club, located directly across from Terminals 1, 2, and 3. Travelers who are not staying at the hotel can use this service for a small fee.
  • For those yogi travelers out there, Chicago Midway International Airport (MDW) has yoga rooms ready for your vinyasas. Located in Concourse C, it is open daily from 6:00 a.m. to 10:00 p.m. and has complimentary mats available for your use.
  • When purchasing flights to Chicago, travelers have two main airport options: the larger and newer O’Hare International Airport (ORD) and the more budget-friendly Midway International Airport (MDW). O’Hare International Airport (ORD) is located on the northwest side of Chicago and offers direct flights to over 200 destinations across the world. Once known as the “busiest square mile in the world”, Chicago Midway International Airport (MDW) is now predominantly serviced by low-cost airlines.
  • If you are flying into Chicago, you will most likely be flying into O’Hare International Airport (ORD) as this is the biggest airport in the city. Chicago is also served by Chicago Midway International Airport (MDW), but this airport is much smaller so flights to this one will be less frequent.
  • When you book your flight to Chicago, it is good to keep in mind that flights to O'Hare International Airport (ORD) will most likely be more frequent than flights to Chicago Midway Airport (MDW). However, there are a few departure points from which there are more departures to Chicago Midway International Airport (MDW), such as from Atlanta.
  • If you are looking at flights to Chicago, an alternative to O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) is the Gary/Chicago International Airport (GYY). Technically just outside Gary, Indiana, the airport is actually only 40 minutes away from downtown Chicago and provides another option for travelers to consider.
  • If you are picking up a rental car when you arrive at Chicago’s O’Hare International Airport (ORD), you will need to make your way to the Multi-Modal Facility where the car rental companies are located. You can access the MMF via the Airport Transit System.

Everything you need to know for your flight to Chicago

Flights with popular airlines flying to Chicago

Flights from the other most popular airlines that fly from the United States to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.