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$21 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 Anywhere departing on 8/22. 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
Sat 8/24
Sat 8/31

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Where can I fly from Chicago?

Prices from CHI, departing Sat 8/24 and returning Sat 8/31

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 (18% of total searches). The next most popular destinations are Las Vegas Harry Reid Intl (9%) and Seattle/Tacoma Intl (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 Paris, Mexico City and Rome.

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 (56% of total searches). The next most popular destinations are Mexico (6%) and Türkiye (4%).

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, Rapid City, Jacksonville, Los Angeles and St. Louis. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Los Angeles at $221, while the most expensive was Rapid City, at $384.

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, 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 Monterrey at $238, while the most expensive was Brussels, at $1,185.

What is the longest direct flight from Chicago?

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

Good to know

Low season

January

High season

March

Cheapest flight

$21
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Chicago O'Hare Airport to Dallas/Fort Worth 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. Owensboro
      from $154 round-trip
    2. Burlington
      from $182 round-trip
    3. Quincy
      from $204 round-trip
    4. Boston
      from $219 round-trip
    5. Trenton
      from $229 round-trip
    6. Detroit
      from $233 round-trip
    7. Atlantic City
      from $236 round-trip
    8. Grand Rapids
      from $238 round-trip
    9. Atlanta
      from $241 round-trip
    10. South Bend
      from $242 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 25% 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 9630 reviews
8.2Boarding
7.9Comfort
8.6Crew
7.4Food
8.0Entertainment
Airline reviews

The boarding was great. With all the delays I was grateful to get on the plane and headed for home. There was no in flight entertainment. Seats were very uncomfortable! Unfortunately we were seated next to an exit row so there was no recline in our seat. Other than that it was a smooth ride.

6.0 GoodKathy, Jul 2024ANC - SLC
Read more about Delta reviews

The boarding was great. With all the delays I was grateful to get on the plane and headed for home. There was no in flight entertainment. Seats were very uncomfortable! Unfortunately we were seated next to an exit row so there was no recline in our seat. Other than that it was a smooth ride.

My flight was cancelled twice and the third time I tried to rebook it online I cancelled the flight because it looked like I would get a refund to my credit card. Instead I now have a credit. I was also on hold for three hours waiting for a representative and then disconnected. I will never fly delta again.

Flight for canceled. Horrible experience.. had to rent a car to drive myself up here.

Flights were terribly delayed. I was at At,anta Airport for over 4 hours waiting for my connection.

My flight consistently said it was on time and the plane didn’t arrive until after 30 minutes after take off and nothing was announced to passengers

The flight was canceled two hours before departure, it took over five hours to rebook us on another flight.

First, the flight was schedule to leave at 12:08. Delayed to 12:38. It is 12:58 and I am sitting at the gate. The staff are not communicating with us (just tell me it’s gonna be five hours if that’s the case, quit hufflepuffing around like you’re trying to board us when the plane isn’t even here and you don’t know where your crew are. I’m still waiting for any communication about the further delay. This is a rebooked flight from a cancelled flight yesterday, when the airline failed to fulfill its fiduciary responsibility to hotel and cover transport for overnight cancelations. Asking about the food on the flight? What food?!? Delta doesn’t serve meals unless you pay for them and you really want me to give delta a high rating for passing out processed snacks (fun size!)? Can we be for real. Delta is cementing itself in history as one of the cheap, stingy, outdated, glory days are over airlines, and it shows. I took this flight knowing delta was going to provide below level service but this is beyond burgers!! I can’t believe a multi billion or dollar company looked straight in my eyes yesterday and I told me this wasn’t their fault and there for the extra cost in hotel and hundreds of dollars in Ubers are MY RESPONSIBILITY. The only thing I am at fault for is believing delta is reputable company worthy of my dollars. I’m not even sure I want to be compensated unless it is cash because I would rather die never traveling again than to put money in their pockets.

The flight was great. The crew were a little terse about the size of my bag. It fit fine.

I know it was not in Deltas fault. But numerous delays and cancelations. I requested a hotel voucher and was told they weren't available. The lady on my hotel shuttle did receive one from American. Why the difference?

Flight was delayed. Had to get rebooked. Diamond medallion but stuck in a crappy seat. Rebooked flight then got delayed again. Then when we finally boarded, we waited another hour for a new crew. Then landed in JFK and sat for another 40 minutes waiting for a crew to come to the gate to be able to deplane. Hot mess all around, which unfortunately is becoming the norm for Delta

Horrible! I paid for a straight flight from Chicago to London. A week before trip it changed and now I had a connecting flight. Our flight was delayed an hour and a half because our flight crew was still flying in from CA. Forty passengers ran from one plane to the next. The next United Airlines flight was delayed two to three hours because of mechanical difficulties. They had to ready another plane which took time. I missed my scheduled excursion in London. 😢

My flight was delayed for a whole day, so I lost a day of my vacation.

United cancelled the flight after a 2 hour delay. The only choice was a 24 hour delay which was then 3 hours delayed.

flight delayed, was put on another flight after standby queue, luggage was misplaced and arrived to me 3 days later

The baggage handlers broke the handle on my bag that they put under the plane that I checked on the jetway. They traded it out for a less quality bag in Tulsa. But, they said they would try to fix it. Bologna! There was no fixing that bag handle. Someone didn’t care how they treated the bag.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

I’ve had a couple flights this week on United that were delayed by an hour or more

Perfect flight. Efficient boarding, on time take off and early arrival. Generally smooth flight.

American is a steady for me. I always get what I expect from them. Sincere effort to get me from one place to another.

BAD. As a family could not sit together. The gate agent told us there was only one seat in the middle left, when we got on the plane the situation was very different with whole rows of seats empty

Plane was delayed an hour causing me to miss my flight to London and now I am not arriving until Sunday instead of Friday. I am stranded at airport and they give me $12 of food vouchers. It's a joke and everyone I talked to was rude

The Airline was not prepared for weather delays. We were held up due to an incoming flight being delayed and so we did not have a flight crew. This caused an extra delay for departure by 2 hours.

When you pay for Premium Economy and you’re promised amenities for the extra money, you expect them to work. They didn’t. USB connector wouldn’t charge continuously. 120v outlet wouldn’t hold anything you plugged into it. The adapter would just fall out. The noise canceling headphones stopped noise cancelling in the first 15 minutes for EVERYONE. No one on the plane knew how to fix it so I couldn’t listen to any movies. I just put in my AirPods and went to sleep. Very unhappy with the crappy Panasonic entertainment system. I won’t buy premium again.

The plane was freezing cold. Normally I’m fine on planes but I needed to toss a sweatshirt on this time.

I missed this flight due to delays on my previous flight.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Original flight delayed several times and finally canceled at 2:30 in the morning. Staff at the gate was not very helpful in resolving problems or communicating why there were delays. I spent 34 hours at the airport before I could leave, they couldn't book me on another early flight even after canceling my original flight. Next flight available after my original flight was canceled was 22 hours later. I will never fly American Airlines again.

On a day with 1000s of worldwide flight cancellations, I was worried about my flight. Not only did my Spirit flight leave as scheduled, but it arrived at destination earlier than expected! This made my day!

The length of delays were extremely frustrating. Stuck in airport for hours. We were to get meal vouchers but it was 3 hours until someone responded to me from their WhatsApp and they said wait for an email. Still no vouchers and it’s been 24 hours. Terrible customer service. The ppl at the gates and bag checkin were miserable and not helpful

Spirit airlines is very bad airline staff doesnt know how to treat passangers they didnt allow us in the flight we reached 45 minutes ago from flight departure but they denied nd said you are late Very disappointed i never reccomend spirit airlines

spirt air lines took advantage of two eighty year olds. we paid extra for cancelation due to health reasons they did not honer they have no spirit. I hope they treat there grand parents beter.

Our flight was delayed four hours and staff did nothing to accommodate the issue.

The flight has been cancelled we have been waiting at the gate for almost 2 hours and they didn't gave me an update for rebooking

I like spirit it make easy for you to travel no matter how your budget it you find cheaper tickets on it, what I don’t understand everything it so expensive a bottle of water cost you price of a case $4 dollars that’s not fair.

Would have been better if I would’ve made it on my flight but it was delayed twice and then canceled and now I’m stuck till Monday which was and extra 5 days I did not count on .

Awful. My flight was three hours late leaving DFW and we just arrived at LAX three hours late and stuck on the runway. I heard the Spirit workers at the desk in DFW say that we were waiting on a crew. I am extremely disappointed in Spirit.

Delays and sending me to different terminal for departures. It looked very confusing and disorganized

Better than expected.on time. Friendly staff in NY however MYR not so nice.

The flight crew and flight attendants are poorly trained and demonstrate poor professionalism. They have a sloppy appearance and communicate with patrons poorly. It is embarrassing for them to be representatives of an airline and for them to be called professionals.

After 5 hours of delay, they cancelled the flight. Very disappointed

My flight to LA was cancelled. I waited at the airport for 3 hrs saying it was delayed and then all of a sudden it was cancelled. Frontier only gave me a voucher and refund but could not rebook me. Flights on other airlines were too expensive last minute. I had to drive down to LA and didn’t even take my return flight home since I had to drive. One of the worst airline experiences in my life. It’s crazy how airlines can just upend people’s plans just like that.

Flying Frontiier was extremely poor!! I paid for a7:15am flight on flight 1601 from PHL To Las Vegas and the delay was brutally, excruciatingly and disgustingly long (8 hrs). I arrived by Uber to PHL at 5:30 am and had to spend the entire 8 hr delay inside the airport. Even more atrocious was that the flight was delayed twice. On the phone with customer service for two hours and was not fully compensated. I feel taken advantage of with this airline. They offered a menial couched for another flight within 90 days to me and my husband who has never flown but this experience has made us almost 100% sure to not fly this airline and will suggest that others don’t either. We don’t want to book ever again, don’t want a menial voucher and I believe by standard and because the flight was delayed for 8 hours, I should be fully reimbursed for the entire round trip. There is no excuse why this should have ever occurred. After sharing my experience with others in Vegas and Philadelphia, I was told that Frontier airlines is notorious for long delayed flights, poor customer service and refusal to compensate people correctly. I’m very nervous to see what departing from Vegas to Philadelphia will bring.

I fly Frontier often and generally don't have any issues. For some reason, the Denver to Houston's George Bush Intercontinental (IAH) flight always needs to wait on the tarmac in Houston because a gate is not available after landing. I've been stuck for as little as 15 minutes and as much as a little over an hour. I know only fly the Frontier Denver to IAH route when there is not an available flight to Houston Hobby (HOU).

Flight was 3 hours late leaving. Poor communication from the staff about delays. Impossible to get in touch with customer service (by design). And it actually didn't come out to be much cheaper than a non-budget airline! Not worth the headache, I'm never flying Frontier again

I’ve never flown frontier without a flight getting canceled. I understand that things go wrong with planes, but all other airlines handle cancellations so well. Frontier becomes a dumpster fire if a problem appears for them.

Checking in was easy and simple, crew was nice and efficient, but I would improve seat assignment randomness to make it easier to sit together based on when you check in. Overall would fly with them again.

Flying Frontier was a nightmare. From the booking through Kayak, checking in, departing and arriving, I will never recommend Kayak or Frontier.

Book cheap domestic flights from Chicago

Recent round-trip flight deals

8/27Tue
nonstopSpirit Airlines
2h 07mORD-LGA
8/28Wed
nonstopSpirit Airlines
2h 32mLGA-ORD
$45
8/21Wed
nonstopSpirit Airlines
2h 29mORD-DFW
8/28Wed
nonstopSpirit Airlines
2h 29mDFW-ORD
$49
10/22Tue
nonstopFrontier
2h 37mORD-DFW
10/29Tue
nonstopFrontier
2h 41mDFW-ORD
$50
8/15Thu
nonstopFrontier
2h 32mORD-DFW
8/19Mon
nonstopFrontier
2h 37mDFW-ORD
$57
9/5Thu
nonstopDelta
2h 41mORD-JFK
9/8Sun
1 stopDelta
6h 12mJFK-ORD
$99
8/24Sat
nonstopDelta
2h 41mORD-JFK
8/26Mon
nonstopDelta
3h 02mJFK-ORD
$104
8/21Wed
nonstopAmerican Airlines
2h 21mORD-JFK
8/23Fri
nonstopAmerican Airlines
2h 39mJFK-ORD
$149
8/6Tue
nonstopAmerican Airlines
2h 21mORD-JFK
8/13Tue
nonstopAmerican Airlines
2h 39mJFK-ORD
$181
8/21Wed
nonstopUnited Airlines
2h 18mORD-LGA
8/28Wed
nonstopUnited Airlines
2h 35mLGA-ORD
$197
8/4Sun
nonstopUnited Airlines
2h 22mORD-EWR
8/5Mon
nonstopUnited Airlines
2h 37mEWR-ORD
$201

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Recent one-way flight deals

8/22Thu
nonstopFrontier
2h 33mORD-DFW
$21
8/27Tue
nonstopSpirit Airlines
2h 07mORD-LGA
$25
10/22Tue
nonstopDelta
2h 25mORD-JFK
$69
9/7Sat
nonstopAlaska Airlines
4h 34mORD-SEA
$77
9/24Tue
1 stopDelta
6h 48mORD-EWR
$79
9/25Wed
nonstopAlaska Airlines
4h 34mORD-SEA
$79
8/26Mon
nonstopAmerican Airlines
2h 18mORD-EWR
$85
10/15Tue
nonstopAmerican Airlines
2h 08mORD-EWR
$87
8/28Wed
nonstopUnited Airlines
4h 33mORD-SEA
$97
9/8Sun
nonstopUnited Airlines
2h 14mORD-EWR
$99

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Last minute flights from Chicago to Anywhere

Last minute flight, train and bus deals

7/30Tue
nonstopSpirit Airlines
3h 18mORD-MIA
8/13Tue
nonstopSpirit Airlines
3h 29mMIA-ORD
$98
7/30Tue
nonstopSpirit Airlines
2h 18mORD-LGA
8/13Tue
nonstopSpirit Airlines
2h 38mLGA-ORD
$102
7/30Tue
nonstopFrontier
2h 35mORD-DFW
8/6Tue
nonstopFrontier
2h 34mDFW-ORD
$145
7/30Tue
nonstopFrontier
2h 55mORD-MCO
8/6Tue
nonstopFrontier
3h 02mMCO-ORD
$151
7/30Tue
nonstopDelta
2h 12mORD-LGA
8/3Sat
nonstopDelta
2h 59mLGA-ORD
$194
7/30Tue
nonstopAmerican Airlines
2h 22mORD-JFK
8/1Thu
multi-stopAmerican Airlines
4h 37mJFK-ORD
$221
7/30Tue
nonstopDelta
2h 14mORD-LGA
7/31Wed
nonstopDelta
2h 29mLGA-ORD
$231
7/30Tue
nonstopUnited Airlines
2h 32mORD-EWR
8/6Tue
multi-stopUnited Airlines
4h 10mEWR-ORD
$261
7/30Tue
nonstopAmerican Airlines
2h 10mORD-EWR
8/2Fri
nonstopAmerican Airlines
2h 37mEWR-ORD
$264
7/30Tue
multi-stopUnited Airlines
4h 24mORD-EWR
7/31Wed
multi-stopUnited Airlines
5h 14mEWR-ORD
$333

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Book cheap international flights from Chicago

Recent round-trip flight deals

9/23Mon
nonstopSpirit Airlines
3h 40mORD-CUN
9/25Wed
nonstopSpirit Airlines
4h 01mCUN-ORD
$179
9/23Mon
nonstopSpirit Airlines
3h 40mORD-CUN
9/25Wed
nonstopSpirit Airlines
4h 01mCUN-ORD
$180
9/8Sun
nonstopFrontier
4h 02mORD-CUN
9/13Fri
nonstopFrontier
4h 01mCUN-ORD
$181
9/9Mon
nonstopFrontier
3h 44mORD-CUN
9/13Fri
nonstopFrontier
4h 09mCUN-ORD
$183
12/2Mon
multi-stopAmerican Airlines
6h 44mORD-CUN
12/6Fri
multi-stopAmerican Airlines
8h 16mCUN-ORD
$306
1/19Sun
multi-stopAmerican Airlines
10h 51mORD-CUN
1/22Wed
multi-stopAmerican Airlines
10h 18mCUN-ORD
$326
9/7Sat
multi-stopDelta
12h 40mMDW-CUN
9/13Fri
multi-stopDelta
12h 23mCUN-MDW
$386
9/21Sat
multi-stopDelta
10h 37mMDW-CUN
9/24Tue
multi-stopDelta
12h 23mCUN-MDW
$391
1/18Sat
multi-stopVolaris
13h 18mMDW-CUN
1/21Tue
multi-stopVolaris
12h 59mCUN-MDW
$454
1/15Wed
multi-stopVolaris
11h 29mMDW-CUN
1/19Sun
multi-stopVolaris
12h 54mCUN-MDW
$469

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Recent one-way flight deals

8/26Mon
nonstopAmerican Airlines
3h 50mORD-CUN
$73
8/13Tue
nonstopFrontier
3h 49mORD-CUN
$78
9/24Tue
nonstopFrontier
4h 02mORD-CUN
$79
8/21Wed
nonstopSpirit Airlines
3h 31mORD-CUN
$83
8/24Sat
nonstopSpirit Airlines
3h 31mORD-CUN
$86
7/30Tue
nonstopAmerican Airlines
3h 55mORD-CUN
$133
8/26Mon
multi-stopVolaris
10h 46mORD-CUN
$169
8/24Sat
multi-stopVolaris
13h 18mORD-CUN
$170
11/29Fri
multi-stopDelta
9h 18mORD-CUN
$177
1/16Thu
multi-stopDelta
10h 26mMDW-CUN
$187

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Flights from Chicago to Anywhere

Return flight deals:

Anywhere - Chicago

Cabin classes:

$172
$177
$237
$39