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Find deals on flights from Chicago from $32

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Anywhere departing on 5/14. 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.
1 adult
0 bags
Tue 5/28
Tue 6/4

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Where can I fly from Chicago?

Prices from CHI, departing Tue 5/28 and returning Tue 6/4

Flights from Chicago - Travel Insights & Trends

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 (15% of total searches). The next most popular destinations are Las Vegas Harry Reid Intl (8%) and Seattle/Tacoma Intl (7%).

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 Tokyo, Paris and Mexico City.

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 price for the route clicked by KAYAK users in the last 2 weeks.
Based on KAYAK flight searches, the most countries to fly to from Chicago is United States (52% of total searches). The next most popular destinations are Mexico (6%) and United Kingdom (3%).

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 Rapid City, Jacksonville, Los Angeles, Honolulu and Fayetteville. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Los Angeles at $230, while the most expensive was Honolulu, at $470.

Which international cities can I fly to direct from Chicago?

There are many international destinations you can fly to non-stop from Chicago. The most popular international destinations from KAYAK users are Paris, Puerto Vallarta, Guadalajara, Morelia and Guatemala City. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Morelia at $195, while the most expensive was Paris, at $866.

What is the longest direct flight from Chicago?

The longest direct flight you can take from Chicago is to Taipei City Taiwan Taoyuan Intl Airport, with a duration of 15h 50m. The next longest is Hong Kong at 15h 40m, followed by a flight to Seoul at 14h 30m.

Good to know

Low season

January

High season

March

Cheapest flight

$32
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Chicago O'Hare Airport to New York LaGuardia Airport

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.

  • Where can I fly to for cheap from Chicago?

    10 cheap destinations to fly to from Chicago
    1. Marion
      from $145 round-trip
    2. Punta Gorda
      from $186 round-trip
    3. Burlington
      from $210 round-trip
    4. Atlanta
      from $211 round-trip
    5. Charleston
      from $246 round-trip
    6. Islip
      from $239 round-trip
    7. Trenton
      from $240 round-trip
    8. Grand Rapids
      from $249 round-trip
    9. Omaha
      from $249 round-trip
  • 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 travelers 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 round-trip 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.

See more FAQs

Top tips for finding a cheap flight out of Chicago

  • Morning departure is around 17% more expensive than an evening flight, on average*.
  • 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.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from Chicago to Anywhere

 
Need help choosing which airline to fly with from Chicago to Anywhere? 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.
8.0
DeltaOverall score based on 10932 reviews
8.0entertainment
7.9comfort
8.2boarding
7.4food
8.6crew
Airline reviews

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

10.0 ExcellentAlexander, Apr 2024RDU - CVG
Read more about Delta reviews

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

my seat got changed twice after checking on then boarding it had been given to a family so by the time they found a seat for me no overhead storage left. i ended up losing my Sony Headphones case because i could even access underthe seat in front of my when deplaning.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries. They dont really bother you about carry-on size, I brought a descent sized backpack and they didnt even check.

Spirit canceled the flight in March and never notified me!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

I do not like the customer service, I had an emergency and needed to cancel a pet reservation right after I had booked it and they would not do anything but issue a credit. I haven't flown in years as I have 7 kids and don't have spare time. I want my $125 back on my card please

Spirit airline tries to screw you at every opportunity. Spirit wanted 65$ for an extra pound in the suitcase Made me open the suitcase at the counter to remove 1 pound. Staff very cold and rude Will never fly spirit again and will recommend same to family and friends

Delayed..4 times...completely disorganized boarding. After 5 hours they scrambled to move ppl off plane bc they overbooked. Then they didn't have a cabin crew. WiFi on plane didn't work. Zero amenities. Once we boarded we sat on tarmac for an hour. Explore all alternate options including purchasing a pair of hiking boots and walking to your destination instead of flying spirit.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

Book cheap domestic flights from Chicago

Recent round-trip flight deals

5/8Wed
nonstopSpirit Airlines
3h 19mORD-MIA
5/11Sat
nonstopSpirit Airlines
3h 27mMIA-ORD
$39
5/8Wed
nonstopSpirit Airlines
2h 11mORD-LGA
5/8Wed
nonstopSpirit Airlines
2h 37mLGA-ORD
$40
5/7Tue
nonstopFrontier
2h 55mORD-MCO
5/10Fri
nonstopFrontier
3h 04mMCO-ORD
$82
5/26Sun
nonstopFrontier
2h 58mORD-MCO
5/29Wed
nonstopFrontier
3h 09mMCO-ORD
$84
7/3Wed
nonstopDelta
2h 09mORD-LGA
7/10Wed
nonstopDelta
2h 34mLGA-ORD
$127
6/26Wed
nonstopDelta
2h 13mORD-LGA
7/1Mon
nonstopDelta
2h 50mLGA-ORD
$133
5/24Fri
nonstopAmerican Airlines
2h 03mORD-LGA
5/26Sun
nonstopAmerican Airlines
2h 35mLGA-ORD
$143
5/29Wed
nonstopAmerican Airlines
2h 13mORD-JFK
6/11Tue
nonstopAmerican Airlines
2h 57mJFK-ORD
$158
5/20Mon
nonstopUnited Airlines
2h 14mORD-LGA
5/21Tue
nonstopUnited Airlines
2h 40mLGA-ORD
$173
5/31Fri
nonstopUnited Airlines
2h 35mORD-BOS
6/3Mon
nonstopUnited Airlines
2h 50mBOS-ORD
$178

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Recent one-way flight deals

5/14Tue
1 stopSpirit Airlines
13h 02mORD-LGA
$26
5/29Wed
nonstopSpirit Airlines
2h 49mORD-MCO
$26
5/7Tue
nonstopFrontier
2h 55mORD-MCO
$35
5/8Wed
nonstopFrontier
2h 56mORD-MCO
$38
7/2Tue
nonstopDelta
2h 13mORD-LGA
$64
7/16Tue
nonstopDelta
2h 14mORD-JFK
$64
5/30Thu
nonstopAmerican Airlines
3h 05mORD-MIA
$70
5/31Fri
nonstopAmerican Airlines
2h 03mORD-LGA
$84
5/26Sun
nonstopUnited Airlines
2h 21mORD-LGA
$98
5/4Sat
1 stopUnited Airlines
6h 14mORD-MIA
$99

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Last minute flights from Chicago to Anywhere

Last minute flight, train and bus deals

5/1Wed
nonstop
2h 53mORD-MCO
5/11Sat
nonstop
3h 04mMCO-ORD
$112
5/3Fri
nonstopSpirit Airlines
3h 15mORD-MIA
5/7Tue
nonstopSpirit Airlines
3h 28mMIA-ORD
$114
5/2Thu
multi-stopFrontier
16h 40mORD-LGA
5/7Tue
multi-stopFrontier
7h 37mLGA-ORD
$142
5/3Fri
nonstopFrontier
2h 56mORD-MCO
5/3Fri
nonstopFrontier
3h 04mMCO-ORD
$164
5/3Fri
nonstopAmerican Airlines
2h 26mORD-BOS
5/12Sun
nonstopAmerican Airlines
2h 52mBOS-ORD
$194
5/3Fri
nonstopAmerican Airlines
2h 17mORD-JFK
6/1Sat
nonstopAmerican Airlines
3h 02mJFK-ORD
$198
5/3Fri
nonstopDelta
2h 14mORD-LGA
5/5Sun
nonstopDelta
2h 47mLGA-ORD
$207
5/3Fri
nonstopUnited Airlines
2h 21mORD-BOS
5/4Sat
multi-stopUnited Airlines
6h 39mBOS-ORD
$218
5/3Fri
nonstopDelta
2h 14mORD-JFK
5/3Fri
nonstopDelta
2h 55mJFK-ORD
$262
4/29Mon
multi-stopUnited Airlines
15h 40mORD-EWR
4/30Tue
nonstopUnited Airlines
2h 40mEWR-ORD
$350

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Book cheap international flights from Chicago

Recent round-trip flight deals

5/12Sun
nonstopSpirit Airlines
3h 32mORD-CUN
5/15Wed
nonstopSpirit Airlines
4h 00mCUN-ORD
$179
5/28Tue
multi-stopSpirit Airlines
6h 16mORD-CUN
6/4Tue
multi-stopSpirit Airlines
15h 56mCUN-ORD
$183
5/19Sun
nonstopSpirit Airlines
3h 32mORD-CUN
5/24Fri
nonstopSpirit Airlines
4h 00mCUN-ORD
$189
5/20Mon
nonstopSpirit Airlines
3h 32mORD-CUN
5/24Fri
nonstopSpirit Airlines
4h 00mCUN-ORD
$190
5/5Sun
nonstopFrontier
4h 08mORD-CUN
5/9Thu
nonstopFrontier
4h 06mCUN-ORD
$194
5/8Wed
nonstopFrontier
4h 08mORD-CUN
5/13Mon
multi-stopFrontier
24h 16mCUN-ORD
$204
5/4Sat
multi-stop
10h 06mORD-CUN
5/9Thu
nonstop
4h 00mCUN-ORD
$211
5/1Wed
nonstop
3h 44mORD-CUN
5/4Sat
multi-stop
8h 34mCUN-ORD
$217
5/20Mon
multi-stopAmerican Airlines
5h 55mORD-CUN
5/25Sat
multi-stopAmerican Airlines
9h 04mCUN-ORD
$312
7/13Sat
multi-stopDelta
9h 42mMDW-CUN
7/17Wed
multi-stopDelta
9h 44mCUN-MDW
$403

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Recent one-way flight deals

4/30Tue
nonstopSpirit Airlines
3h 44mORD-CUN
$85
5/28Tue
multi-stopSpirit Airlines
6h 16mORD-CUN
$86
5/14Tue
multi-stopFrontier
9h 06mMDW-CUN
$93
5/11Sat
multi-stopFrontier
11h 12mMDW-CUN
$97
5/2Thu
multi-stopAmerican Airlines
12h 40mORD-CUN
$164
7/2Tue
multi-stopAmerican Airlines
6h 45mORD-CUN
$168
5/2Thu
multi-stopUnited Airlines
24h 30mORD-CUN
$179
5/3Fri
multi-stopDelta
7h 38mMDW-CUN
$180
5/3Fri
multi-stopDelta
12h 58mORD-CUN
$180
6/16Sun
multi-stopUnited Airlines
24h 36mORD-CUN
$195

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Flights from Chicago to Anywhere

Return flight deals:

Anywhere - Chicago

Cabin classes:

$311
$328
$277
$32