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Find Cheap Flights from Chicago

Where can I fly from Chicago?Prices from CHI, departing Fri 8/29 and returning Fri 9/5
Booking Insights

KAYAK's insights & trends for flights from Chicago

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

Which are the most popular places to fly to from Chicago?

The domestic destinations KAYAK users have most searched for when searching for flights from Chicago.
Based on KAYAK flight searches, the most popular place to fly from Chicago is New York (37% of total searches). The next most popular destinations are Washington, D.C. (31%) and Raleigh-Durham (6%).

What are the most popular international flights out of Chicago?

The international destinations KAYAK users have most searched for when searching for flights from Chicago.
There are many international destinations you can fly to from Chicago. The most popular international destinations among KAYAK users are Cairns, Adelaide and Perth.

What are the most popular countries to fly to from Chicago?

The most popular countries KAYAK users have searched for from Chicago along with the average round-trip price for the route clicked by KAYAK users in the last 2 weeks.
Based on KAYAK flight searches, the most popular country to fly to from Chicago is India (18% of total searches). The next most popular destinations are Turkey (14%) and Canada (12%).

What is the longest direct flight from Chicago?

The longest direct flight you can take from Chicago is to New Delhi, with a duration of 16h 20m. The next longest is Hong Kong at 15h 50m, followed by a flight to Taipei City Taiwan Taoyuan Intl Airport at 15h 00m.

Good to know

Low seasonApril
Best time to beat the crowds (10% less expensive on average)
Most popular time to fly (34% more expensive on average)

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

Insights shared by verified travellers who flew from Chicago to anywhere 
Verified travelerFlew with British AirwaysORD-LHRJune 2025
Get a wheel chair if you have difficulty walking
RogerFlew with Japan AirlinesORD-PITJune 2025
Make sure when you go from one airline to another that your bag is marked properly so they can get it on the right damn airplane. I did that and it still didn’t make it.
Verified travelerFlew with United AirlinesORD-LASMar 2025
If you can select your seats in advance please do
JoeFlew with IberiaORD-LHRApr 2025
Get there early. Nice airport options while you wait.
Verified travelerFlew with IberiaORD-LHRMay 2025
Get to the airport early so you’re relaxed. Con yourself into believing it’s bedtime and try to sleep so that you can keep going all day when you get there. If you can afford more comfy seats it might be worth it - though I always have the cheap ones so I can’t say for sure. Try very hard not to. sit in the middle. I’m small and the guy next to me played games all night and didn’t care that he continually ( with every move) jabbed me with his arm. This was my first flight with Cheap Flights and it was far less convenient than other times I’ve flown overseas.
AndreaFlew with United AirlinesORD-ATLMay 2025
Ask for stewards to assist and provide amenities or you won’t get them.
Verified travelerFlew with EVA AirORD-TPEFeb 2025
Coming from Chicago which is also a busy airport, I recommend checking in online prior to thetrip. Make sure luggages follow the required weight and go directly bag drop. You may also want for the attendants to print your boarding pass with the recent details on boarding gate number and zoning.
Verified travelerFlew with ANAORD-HNDJan 2025
Consider light carry-ons to give yourself stretch room for economy and quick onboarding and off boarding especially with connecting flights.
TFlew with Scandinavian AirlinesORD-CPHJan 2025
Don’t forget you can pinch and slide the headrest up and down for maximum sleeping comfort.
Verified travelerFlew with American AirlinesORD-TPADec 2024
I recommend having movies and songs downloaded on your device.
DarylFlew with Cathay PacificORD-HKGJan 2025
They are strict with carry on and they weigh it upon check in.
JanieFlew with SWISSORD-PHXFeb 2025
I think you should prebook food or bring your own food.
valerieFlew with Air CanadaORD-YULJan 2025
“Meal” usually means more than a light snack. I thought what they served was an appetizer not the total meal. So I’d eat before or bring food.
Verified travelerFlew with Spirit AirlinesORD-LASSept 2024
Make sure you get your seats booked at time of booking or at the least when you check in and make sure you check in at the earliest to have preferred seating.
MikeFlew with American AirlinesORD-LAXSept 2024
Arrive early, grab a bottle of soda before getting on the plane and open it in the terminal. If you wait until flying the pressure will decarbonize the drink.
Verified travelerFlew with SWISSORD-ZRHSept 2024
Bring a neck pillow and a heavy sweater bc it does get cold. I used the blanket for my legs. Also: get a seat in the aisle.
Verified travelerFlew with Alaska AirlinesORD-PDXSept 2024
Not many amenities at the terminal. I would suggest grabbing anything that catches your eye before you get all the way down. There weren't a lot of Alaska flights out of Chicago, and we were at the extreme end of the terminal.
Verified travelerFlew with Cathay PacificORD-HKGNov 2024
First flight to hkg but been to asia many times. Most airlines have frequent beverage service to combat the dehydration that comes with a long flight.
DevikaFlew with Etihad AirwaysORD-AUHSept 2024
I wish I had known how much walking I had to do to the transfer terminal from landing to transfer gate.
Verified travelerFlew with Porter AirlinesMDW-YTZSept 2024
Please start bags check-in at least 2.5 hour before flight and finish at 30 min before flight.
Verified travelerFlew with United AirlinesORD-FRASept 2024
Be prepared to wait in long line for boarder control. Allow enough time for your layover
mauriceFlew with IberiaORD-JFKSept 2024
You should arrive early, take a lighht snack and be prepared for delays.
RuthFlew with United AirlinesORD-AMSOct 2024
Facial recognition seemed to slow boarding down, not speed it up. Why don’t airlines board from the back to the front? That would certainly speed things up!
HeatherFlew with LufthansaORD-MKEAug 2024
Make sure there's enough time between connections to go through customs and recheck your luggage. They will not let you proceed so you can't even try to run and catch the flight if you want to.
WilliamFlew with EVA AirORD-TPEJuly 2024
Wear compression socks or prepare for massive swelling of your feet and ankles.
MikeFlew with British AirwaysORD-FCOJune 2024
Make sure you check the plane type and economy seating space.
EstherFlew with Ethiopian AirORD-ADDAug 2024
Eat before boarding the food is smelly. Do not sit near a toilet
Verified travelerFlew with United AirlinesORD-PHXApr 2024
Use the find my gate feature on the flights phone app if available as the airport is a bit confusing
AyannaFlew with Spirit AirlinesORD-TPAMay 2024
Fly out of Midway airport instead of O'Hare because its smaller and easier to manage.
PaulFlew with Alaska AirlinesORD-SEAApr 2024
The flight is long, at over four hours. I would try to get a window or aisle seat to be more comfortable. I would check with other airlines that allow you to choose your seat even if you are in the economy section. I would bring your own food on the plane as the service was sometimes sketchy.
Verified travelerFlew with Alaska AirlinesORD-SEAApr 2024
If you miss your flight ask any alaska agent to how and where to rebook the flight.
FreddieFlew with IcelandairORD-KEFMay 2024
If you’re in business class board first to avoid queuing
UzomaFlew with American AirlinesORD-DCAJan 2024
ORD and DCA are nice airports with plenty of space. ORD is always busy so allow ample time to drive there, drop your bag, and go through security if you don't have TSA pre check.
RogerFlew with ANAORD-HNDFeb 2024
The extra leg room and been able to recline better is worth the extra money. I bidding on the premium and offered the least they would accept and got it.
AaronFlew with American AirlinesORD-LHRDec 2023
Find a flight where you are allowed to choose your seats before the day of boarding for anything international.
RyanFlew with EVA AirORD-TPEJan 2024
Bring things to make the seats more comfortable
Verified travelerFlew with United AirlinesORD-YOWJan 2024
I always expect issues with United but there doesn't seem to be another airline to use. Advice: Give yourself and extra day to get anywhere - don't be in a hurry to get home either.

FAQs for booking flights out of Chicago

  • Does Midway International Airport have an on-site hotel?

    While Midway International Airport does not have an on-site hotel, there are several hotels are nearby. For example, the Holiday Inn Express & Suites Chicago Midway Airport is less than 5 minutes from the airport and has a free shuttle, while the Hilton Garden Inn Chicago Midway Airport is a 3-minute drive from the airport.

  • What lounges are available in Chicago O’Hare International Airport?

    There are a few different lounges to choose from at Chicago O’Hare International Airport, including the American Airlines Admirals Club, which is in Concourses G, H, K, and L. There is also the United Club in Concourses B and C, as well as the Delta Sky Club in Terminal 2.

  • What options are there for traveling from the city center to Midway International Airport?

    If you choose to drive from Downtown Chicago to Midway International Airport, the trip will typically take you around 15 to 20 minutes in total. You can also opt to use public transportation instead, such as the Orange subway line, which will typically take you between 30 and 35 minutes. A one-way ticket will cost you approximately $2.50.

  • Does Chicago O’Hare International Airport offer any facilities for those traveling with pets?

    If you are flying out of Chicago O’Hare International Airport with a pet, keep in mind that there are several indoor and outdoor pet relief areas available. These are equipped with sitting areas, trash cans, and free plastic bags.

  • What are the names of Chicago’s airports?

    All flights from Chicago depart from one of Chicago O'Hare Intl Airport, Chicago Midway Airport or Chicago Greater Rockford Airport. Chicago O'Hare Intl Airport’s airport code is ORD. It can also be referred to as Chicago O'Hare, O'Hare Intl. Chicago Midway Airport’s airport code is MDW. It can also be referred to as Chicago Midway, Chicago Midway Intl, Midway, Midway Intl. Chicago Greater Rockford Airport’s airport code is RFD. It can also be referred to as Chicago Rockford Intl, Greater Rockford.

  • How does KAYAK find such low prices on flights from 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 from Chicago.

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

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

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

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

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from 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 from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding a cheap flight out of Chicago

  • There are two primary airports in Chicago, Chicago O’Hare International Airport (ORD) and Midway International Airport (MDW). While Chicago O’Hare International Airport can be found just under 15 miles north of the city center, Midway International Airport is approximately 8 miles south of Downtown Chicago.
  • Chicago O’Hare International Airport is a major hub for airlines such as American Airlines and United Airlines, so it’s not uncommon for these companies to operate flights departing from this airport. Likewise, Midway International Airport is a hub for Southwest Airlines, so you’ll see that this airline commonly services trips from here.
  • If you have extra time before your flight boards at Chicago O’Hare International Airport, you can fit in a workout at the Hilton Athletic Club. Located in Terminal 2, it is equipped with facilities such as a steam room, sauna, and lap pool. There is also a yoga room in Terminal 3 open to all passengers for free.
  • Midway International Airport offers a few different services for those flying with children, such as a baby care room in Concourse C designed to give parents a private area to nurse their little ones. There is also a designated security lane for families.
  • If you feel like treating yourself before a long day of traveling, head to one of the Terminal Getaway Spa locations in Terminals 3 and 5 of Chicago O’Hare International Airport. Here, you can receive a variety of massages, manicures, pedicures, and facials.

Reviews of the top 3 airlines flying from Chicago to Worldwide

 
Need help choosing which airline to fly with from Chicago to Worldwide? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.5
Qantas AirwaysOverall score based on 887 reviews
7.7Boarding
7.2Entertainment
6.9Food
7.4Comfort
8.2Crew
Airline reviews

Poor! This flight was delayed 14 hours. There was no assistance in helping customers find other routes to their destination, nor any other kind of support. It was a chaotic experience. I'm not likely to fly with AA going forward.

2.0 MediocreAnonymous, July 2025LAX - ORD
Read more Qantas Airways reviews

Poor! This flight was delayed 14 hours. There was no assistance in helping customers find other routes to their destination, nor any other kind of support. It was a chaotic experience. I'm not likely to fly with AA going forward.

Business class points redemption - good value for points paid, dubious value if out of your own pocket, domestic class business product okay for this length of flight. The flight left and arrived on time, crew were good, aircraft was a bit old and tired, but still miles ahead of their competitors in Virgin and Jetstar.

Five hour flight instead of four hours due to westerly headwinds which wasn’t the fault of Qantas !

One of the oldest most uncomfortable "lay down" seats I've ever experienced. Old plane and old seats that don't lay flat. The seat back does not even recline - at all. Instead the legrest awkwardly extends to fill the gap between a small cubby into which you must insert your feet/legs. I am 5' 11" and could not lay straight but had to tuck my knees. Ticket was also very expensive. Would not recommend flying business/first on Finair from Melbourne to Bangkok and will not do so again myself.

Was bumped to a later flight because of inefficiency on part of the airline.

Touch screens were very difficult to use, generally being laggy and unresponsive- it was quite an art to get it to play the thing you wanted rather than some thing at random. Selection of films and Tv was good when touchscreen decided to finally respond.

Loved the staff. The economy seats could have been bigger.

Their aircraft are old and amenities lack way behind other international carriers leaving from BNE. Even in economy

I liked the service, the menu, and the comfort of the seats! Even tho we were seated by the bathrooms, the reclining seats and movie selection was very good, my husband and I didn’t mind at all

Complaint is with American Airlines which delayed our flight from salt lake to Dallas reaulting in us missing our connection to Brisbane. Had to spend 24 hours in Dallas to wait for the next flight. Awful experience and ruined my wife’s birthday.

Both flights are delayed so I rate the whole experience as mediocre.

I booked my flight months ago, and checked-in online about 12 hours before the flight. I received an email confirmation of check-in. I had no subsequent communication from Air Canada after my original booking. After arriving at the airport three hours before the flight, as instructed, I waited 90 minutes for an agent to appear to check my bag. I was informed that my flight had been canceled many weeks before, and that flight was no longer being run!! I showed a copy of my check-in confirmation, but no explanation could be found. I was placed on standby for the next flight and the connection. Luckily, those flights were not full and I arrived at my destination. I double checked my email, but I received no update about the flight from Air Canada until the day of the flight.

I had a good experience. I liked being informed about the status of my luggage

Very bad service the way back we was on the way for r two days very bad condition and waiting for luggage till now

I was forcefully re-routed to another destination and was delayed a total of 8hours. I have still not received my bags, no one is taking responsibility. The agents at the airport lied to me that I will get to my destination same time as my previous flight where I was forcefully re-routed from.

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

Our flight was canceled at the last minute. Someone on the flight said the exact same thing happened to her the day before. I will say they helped us book a flight on another airline so that we could still make our vacation with little delay.

United had no (zero) record of our flight. It took over an hour of us standing in line with surly employee while others waited to get resolved. I have never experienced such poor service and poor empathy.

We had a very long delay. First the inbound flight took a while, then maintenance, they “fixed it” to then do boarding and leave the gate, and waste a lot of time to have to go back to the gate and eventually deplane. Had to wait for a new aircraft, wait for a gate, and do the whole thing again. Instead of leaving at 9:50am we left until past 1. I could’ve not woken up at 5am, or spend some more time with my family if they gave more grace period of time between flights to give some time in case of any issues. But they have to make all and every dollar possible

Aircraft had technical issues. After 3 hours of trying to resolve, flight was cancelled. Was booked on a flight leaving 12 hours after intended departure. Now on 4 flights instead of 2 and a day late to my destination.

The flight was 3.5 hrs delayed. I was not notified prior to arriving to the airport via spirit app. or via boarding pass that I already had loaded on my phone. The agent that i saw at the counter didn’t mention anything about the delay either. I only saw the update after logging in to my email account.

The flight and boarding process was smooth. Wifi was unavailable and I prepaid for it. Have requested a refund

Had a issue with catching flight due to airline, was unable to board flight

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

Not great. Seats uncomfortable. Crew a little rude. Amenities like wifi and drinks way too expensive.

Late departure by 1:45min. No explanation why. During boarding inconsistent policing of their baggage rules. Before takeoff and lamdimg strange obsession with window shade and armrest positions. Don't know why they care. 15 min tarmac delay on arrival, they blamed airport congestion but we were the o lh flight waiting, it was clear it was due to poor staff planning (only one ground crew to receive airplanes and multiple arrivals) Got there but was rrally lame the whole trip.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

We sat on the tarmac for an hour waiting for a gate to deplane.

Friendly employees, good seat, on time, Great flight. Pilot and attendants greeted passengers as we deplaned. However, I could not ever understand what the flight attendant was saying on the mic. It was too fast, and too loud.

Everything was fine, but there was no food or entertainment, so I didn’t know how to rate that.

Everything you need to know for your flight from Chicago

Cabin class types available on flights from Chicago

Cabin classes available on flights from Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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