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Find Cheap Flights from Chicago

Where can I fly from Chicago?Prices from CHI, departing Sun 10/11 and returning Sun 10/18
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?

Based on KAYAK flight searches, the most popular place to fly from Chicago is New York (50% of total searches). The next most popular destinations are Washington, D.C. (23%) and Raleigh-Durham (5%).

What are the most popular international flights out of Chicago?

There are many international destinations you can fly to from Chicago. The most popular international destinations among KAYAK users are Sydney, Melbourne and Brisbane.

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

Based on KAYAK flight searches, the most popular country to fly to from Chicago is Canada (42% of total searches). The next most popular destinations are United Arab Emirates (37%) and Colombia (21%).

Which cities can I fly to direct from Chicago?

There are loads of places you can fly direct to from Chicago. The most popular destinations for direct flights among KAYAK users are Los Angeles and San Francisco. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was San Francisco at $256, while the most expensive was Los Angeles, at $666.

What is the longest direct flight from Chicago?

The longest direct flight you can take from Chicago is to Manila, with a duration of 16h 40m. The next longest is Hong Kong at 16h 00m, followed by a flight to Taipei City Taiwan Taoyuan Intl Airport at 15h 25m.

What are the cheapest places to fly to from Chicago?

The cheapest destination for a flight from Chicago found on KAYAK in the last two weeks was Atlanta, costing $187. The next cheapest destinations were Los Angeles at $206 and Calgary at $242.

Good to know

Low season

August

Cheapest flight

$160
Best time to beat the crowds (6% less expensive on average)
Most popular time to fly (30% more expensive on average)
Flight from Chicago to Newark

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

Insights shared by verified travellers who flew from Chicago to anywhere 
IndivarFlew with American Airlines-Aug 2026
For a work trips, consider booking an Airline with multiple daily flights in case you might want standby for an earlier return flight.
KimberlyFlew with American Airlines-Aug 2026
Get to the airport early if you don’t have Pre-Check!
ScottFlew with Air Canada-June 2026
Make sure you have enough time between connecting flights so ½ of your baggage doesn't miss the flight and take another 24hrs to show up
MarkFlew with United Airlines-July 2026
Order your choice of food in advance on the website. Take snacks as supplement as onboard food is inadequate
Verified travelerFlew with Air Canada-Aug 2026
Pray. Use Apple air tags. That way at least you know where your luggage is
Verified travelerFlew with United Airlines-Aug 2026
Make sure to have at least 2 hours layover because it is a huge airport and the airport is rather inefficient with unfriendly personnel.
MarkFlew with American Airlines-June 2026
Get there early, only one TSA line open and thew queue was very long.
NFlew with United Airlines-July 2026
Only do carry on the checked bag was stressful and time consuming.
Verified travelerFlew with United Airlines-Apr 2026
Make sure your flight has more than three hours as layover if you’re connecting to another flight.
Verified travelerFlew with British Airways-Mar 2026
Take early morning flights to adjust to weather-related delays.
IanFlew with American Airlines-Apr 2026
Lately ORD airport struggles in general often having ground stops. Construction extends travel back to airport so allow 2 hrs. Over past few months, experienced far few delays on United than AA.
MamiFlew with Japan Airlines-May 2026
I did not find particularly good stuff in Entertainment (movies and TV), so you may want to bring what you like.
SteveFlew with Spirit Airlines-Mar 2026
Bring a seat cushion if you're flying Spirit.
Verified travelerFlew with United Airlines-Apr 2026
Chicago airport is super chaotic. We had come in from an overseas flight and were required to get our checked bags at Baggage Claim and recheck them for our next flight, which took a while. Then after going through a LONG customs line (again) and rechecking my bag, I was told to take a shuttle to a different terminal for my final flight. Even though I never left the building and had no access to the outside world, I had to go through security AGAIN (boots off, dump out my water, wait in long lines…) My advice is to be sure you have at least a couple of hours between flights to deal with the insanity.
Verified travelerFlew with American Airlines-Apr 2026
travel to ohare is horror - work in extra time
MarcoFlew with United Airlines-Dec 2025
United delayed my luggage twice on flight to Europe (first flight was for an important event) I carry 2 days of clothes in my backpack no matter who I'm flying with United especially so. No less than 2 hour layover to decrease possibility of loss/delay of luggage. Second EU trip my luggage was left in Germany even though my layover was just over 1 hour. Select layovers of 2+ hours although Unite will sell flights with 40 minutes layover (nonsense). 1 hour layover was not enough to transfer luggage in FRA. The last scan was 30 minutes after the flight left (SMH).
ZacharyFlew with Scandinavian Airlines-Nov 2025
Buy out a row so you have room to sleep.
Verified travelerFlew with British Airways-June 2025
Get a wheel chair if you have difficulty walking
RogerFlew with Japan Airlines-June 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 Airlines-Mar 2025
If you can select your seats in advance please do
JoeFlew with Iberia-Apr 2025
Get there early. Nice airport options while you wait.
Verified travelerFlew with Iberia-May 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 Airlines-May 2025
Ask for stewards to assist and provide amenities or you won’t get them.
Verified travelerFlew with Royal Jordanian-Apr 2025
I think you should choose another airline unless you obligated. Prepare yourself for no wifi The crew are polite but somewhat non co-operative Charge your phone before flight because charging station are non-working
Verified travelerFlew with EVA Air-Feb 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 ANA-Jan 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 Airlines-Jan 2025
Don’t forget you can pinch and slide the headrest up and down for maximum sleeping comfort.
Verified travelerFlew with American Airlines-Dec 2024
I recommend having movies and songs downloaded on your device.
DarylFlew with Cathay Pacific-Jan 2025
They are strict with carry on and they weigh it upon check in.
JanieFlew with SWISS-Feb 2025
I think you should prebook food or bring your own food.
valerieFlew with Air Canada-Jan 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 Airlines-Sept 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 Airlines-Sept 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 SWISS-Sept 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 Airlines-Sept 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 Pacific-Nov 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 Airways-Sept 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 Airlines-Sept 2024
Please start bags check-in at least 2.5 hour before flight and finish at 30 min before flight.
Verified travelerFlew with United Airlines-Sept 2024
Be prepared to wait in long line for boarder control. Allow enough time for your layover
mauriceFlew with Iberia-Sept 2024
You should arrive early, take a lighht snack and be prepared for delays.
Verified travelerFlew with Austrian Airlines-Oct 2024
This Austrian 787-9 plane has very uncomfortable seats. Extremely tight space in economy class. If you can, upgrade to premium economy. Do not select seats close to the restrooms. The plane only has two restrooms center cabin and there’s always a line of people waiting to use the restrooms.
RuthFlew with United Airlines-Oct 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 Lufthansa-Aug 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 Air-July 2024
Wear compression socks or prepare for massive swelling of your feet and ankles.
DianaFlew with American Airlines-July 2024
Be sure to have name spelled correctly. Two hours early works well.
MikeFlew with British Airways-June 2024
Make sure you check the plane type and economy seating space.
EstherFlew with Ethiopian Air-Aug 2024
Eat before boarding the food is smelly. Do not sit near a toilet
Verified travelerFlew with United Airlines-Apr 2024
Use the find my gate feature on the flights phone app if available as the airport is a bit confusing
AyannaFlew with Spirit Airlines-May 2024
Fly out of Midway airport instead of O'Hare because its smaller and easier to manage.
PaulFlew with Alaska Airlines-Apr 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 Airlines-Apr 2024
If you miss your flight ask any alaska agent to how and where to rebook the flight.
FreddieFlew with Icelandair-May 2024
If you’re in business class board first to avoid queuing
UzomaFlew with American Airlines-Jan 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 ANA-Feb 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 Airlines-Dec 2023
Find a flight where you are allowed to choose your seats before the day of boarding for anything international.
RyanFlew with EVA Air-Jan 2024
Bring things to make the seats more comfortable
Verified travelerFlew with United Airlines-Jan 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 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.
7.8
DeltaOverall score based on 8561 reviews
8.5Crew
7.2Food
8.1Boarding
7.8Comfort
7.8Entertainment
Airline reviews

The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

4.0 OkayJeff, Aug 2026
Read more Delta reviews

The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

Despite having numerous passengers held up by American Airlines delays. Qantas (an AA partner) closed boarding with 0 flexibility

Having the computer outage compounded by delayed takeoff while waiting for aircrew (who were also delayed) resulted in me missing my int’l flight

Boarding , crew and meals were all amazing. Couldn't wish for a better LOOONG flight from Dallas to Sydney .

Boarding was effortless, the food was outstanding, the seats in Premium Economy were extremely comfortable, and the staff and crew were excellent.

We had a cancellation due to weather, but the American Airlines staff was very helpful. Once we got on a plane, the trip was great.

PREMIUM ECONOMY - excellent !Brilliant new plane. Excellent tv catalogue. Good food. Good communication and service from all friend Australian crew. Good communication from captain. Best travel experience in years.

I couldn't hear all of the announcements. It was nice when they put them on the screen.

On the Qantas flight, I could barely hear some of the announcements. It was better when I could read them on the screen.

Our boarding and flight was very good. However when we landed and pulled in to the gate it took 55 minutes for the jet bridge to be positioned next to the aircraft. That caused us to miss our ground transportation and it caused us unnecessary last minute transit planning and expense. Our flight was AA1733 on March 17, 2026

I liked boarding the plane. The staff were rude, the food was appalling and the chairs the most uncomfortable I have ever experienced

More options for your flight from Chicago

Complete your trip to Worldwide with a hotel stay or car hire