$42 Find Deals on Flights from Chicago

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 Worldwide departing on 7/9. 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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Find Cheap Flights from Chicago

Where can I fly from Chicago?Prices from CHI, departing 일 7/13 and returning 일 7/20

Book Cheap International Flights from Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from 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 international flight deals from Chicago to anywhere

화, 6월 24 - 토, 6월 28
Spirit Airlines Logo
4:45 pm - 8:03 amORD-CUN
15h 18m1 stop
Spirit Airlines Logo
10:55 am - 2:49 pmCUN-ORD
3h 54mnonstop
$217Spirit Airlines
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화, 7월 8 - 토, 7월 12
Spirit Airlines Logo
7:49 pm - 8:17 amORD-CUN
12h 28m1 stop
Spirit Airlines Logo
10:55 am - 2:49 pmCUN-ORD
3h 54mnonstop
$219Spirit Airlines
Find Deal
화, 7월 8 - 금, 7월 11
Spirit Airlines Logo
5:05 am - 11:21 amORD-CUN
6h 16m1 stop
Spirit Airlines Logo
10:55 am - 2:49 pmCUN-ORD
3h 54mnonstop
$224Spirit Airlines
Find Deal
금, 7월 11 - 월, 7월 14
Spirit Airlines Logo
10:55 am - 2:49 pmCUN-ORD
3h 54mnonstop
Spirit Airlines Logo
6:00 am - 9:50 amORD-CUN
3h 50mnonstop
$225Spirit Airlines
Find Deal
금, 7월 11 - 토, 7월 12
Spirit Airlines Logo
10:55 am - 2:49 pmCUN-ORD
3h 54mnonstop
Spirit Airlines Logo
6:00 am - 9:50 amORD-CUN
3h 50mnonstop
$227Spirit Airlines
Find Deal
금, 7월 11 - 월, 7월 14
Spirit Airlines Logo
10:55 am - 2:49 pmCUN-ORD
3h 54mnonstop
Spirit Airlines Logo
6:00 am - 9:50 amORD-CUN
3h 50mnonstop
$228Spirit Airlines
Find Deal
목, 9월 25 - 화, 9월 30
Delta Logo
1:45 pm - 9:44 pmCUN-MDW
7h 59m1 stop
Delta Logo
1:05 pm - 8:02 pmMDW-CUN
6h 57m1 stop
$275Delta
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금, 9월 19 - 목, 9월 25
Delta Logo
3:07 pm - 9:44 pmCUN-MDW
6h 37m1 stop
Delta Logo
1:05 pm - 8:02 pmMDW-CUN
6h 57m1 stop
$277Delta
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토, 7월 12 - 월, 7월 14
Frontier Logo
9:09 am - 8:22 pmCUN-MDW
11h 13m1 stop
Frontier Logo
6:20 am - 12:27 pmMDW-CUN
6h 07m1 stop
$290Frontier
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수, 8월 13 - 목, 8월 21
 Logo
2:20 pm - 11:55 pmORD-BCN
26h 35m1 stop
 Logo
7:30 pm - 12:10 pmBCN-ORD
23h 40m1 stop

Book Cheap Domestic Flights from Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from 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 domestic flight deals from Chicago

화, 7월 1 - 수, 7월 9
Spirit Airlines Logo
1:43 pm - 6:00 pmORD-MIA
3h 17mnonstop
Spirit Airlines Logo
1:35 pm - 4:11 pmMIA-ORD
3h 36mnonstop
$83Spirit Airlines
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수, 7월 2 - 수, 7월 9
Spirit Airlines Logo
5:51 am - 9:00 amORD-LGA
2h 09mnonstop
Spirit Airlines Logo
6:30 pm - 8:00 pmLGA-ORD
2h 30mnonstop
$85Spirit Airlines
Find Deal
수, 7월 2 - 수, 7월 9
Spirit Airlines Logo
1:43 pm - 6:00 pmORD-MIA
3h 17mnonstop
Spirit Airlines Logo
1:35 pm - 4:11 pmMIA-ORD
3h 36mnonstop
$85Spirit Airlines
Find Deal
수, 7월 2 - 수, 7월 9
Spirit Airlines Logo
7:56 am - 11:40 amORD-MCO
2h 44mnonstop
Spirit Airlines Logo
6:20 pm - 8:28 pmMCO-ORD
3h 08mnonstop
$85Spirit Airlines
Find Deal
화, 7월 1 - 화, 7월 8
Spirit Airlines Logo
9:28 pm - 12:46 amORD-EWR
2h 18mnonstop
Spirit Airlines Logo
5:00 am - 6:37 amEWR-ORD
2h 37mnonstop
$86Spirit Airlines
Find Deal
토, 9월 13 - 화, 9월 16
JetBlue Logo
8:34 am - 12:00 pmORD-JFK
2h 26mnonstop
JetBlue Logo
10:30 am - 12:10 pmJFK-ORD
2h 40mnonstop
$97JetBlue
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화, 8월 19 - 토, 8월 23
JetBlue Logo
6:00 am - 9:12 amORD-JFK
2h 12mnonstop
JetBlue Logo
8:30 pm - 10:28 pmJFK-ORD
2h 58mnonstop
$98JetBlue
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화, 11월 11 - 화, 11월 18
American Airlines Logo
8:05 am - 10:50 amORD-SEA
4h 45mnonstop
American Airlines Logo
11:45 am - 5:45 pmSEA-ORD
4h 00mnonstop
$109American Airlines
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수, 9월 17 - 금, 9월 19
Alaska Airlines Logo
10:00 am - 12:34 pmORD-SEA
4h 34mnonstop
Alaska Airlines Logo
12:59 am - 7:03 amSEA-ORD
4h 04mnonstop
$117Alaska Airlines
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토, 9월 20 - 월, 9월 22
Hawaiian Airlines Logo
6:20 am - 8:50 amORD-SEA
4h 30mnonstop
Hawaiian Airlines Logo
12:59 am - 7:03 amSEA-ORD
4h 04mnonstop
$125Hawaiian Airlines
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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 (19% of total searches). The next most popular destinations are Las Vegas Harry Reid Intl (6%) and Dallas (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 San Juan, Paris and Tokyo.

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 Mexico (10% of total searches). The next most popular destinations are India (8%) and United Kingdom (7%).

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 Traverse City, Jacksonville, Los Angeles, Honolulu and Charlotte. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Los Angeles at $178, while the most expensive was Honolulu, at $509.

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 Brussels, Paris, Guadalajara, Tokyo and Guatemala City. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Guatemala City at $197, while the most expensive was Tokyo, at $2,329.

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 05m. The next longest is Hong Kong at 15h 50m, followed by a flight to Taipei City Taiwan Taoyuan Intl Airport at 15h 05m.

Good to know

Low seasonJanuary
High seasonMarch
Cheapest flight$42
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 8% 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.

  • 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.

Top tips for finding a cheap flight out of Chicago

  • Looking for a cheap flight? 25% of our users found tickets from Chicago to the following destinations at these prices or less: Miami $137 one-way - $112 round-trip
  • 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.

Top 5 airlines serving 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.
8.0
SouthwestOverall score based on 4286 reviews
8.6Crew
7.1Food
8.0Comfort
8.2Boarding
7.6Entertainment
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Good experience except for the drunk woman who was with a child. Sad

The ease of booking the flight was very good. Speaking with customer service was also good. However, the crew people are unfriendly and unwelcoming which I found this as unprofessional. As far as comfort it was mediocre. This was my first time flying Spirit and I chose them because of the flight times met my needs and my budget. However, I would be reluctant to fly on Spirit again. In addition, if the crew were more friendly and at least appeared somewhat happy and welcoming personally it would probably make the experience of flying with Spirit better.

Tell them to chose a better, less bumpy route :( my seat had no window all the way at the end 😔

Seats too hard, too much lumbar. Space between rows was extremely tight, so tight hard to place item under seat in front of me. No tv screens. Zero plugs for charging phones. Too many sales pitches

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

It was horrible. We were not allowed on the flight by spirit staff at the gate during boarding because I had a guitar. The same guitar I had at check in which I paid for and they said I can take it on the plane. We missed our flight, lost our luggage, and had to pay another $900 to rebook flights. Worst travel experience ever and spirit staff are the worst staff ever.

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

I liked the price of the flight and the chance to buy a seat with no person seated in the middle seat.. Also the flight was right on time.

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

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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