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Find deals on flights from Chicago from $26

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 8/28. 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 7/2
Tue 7/9

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Where can I fly from Chicago?

Prices from CHI, departing Tue 7/2 and returning Tue 7/9

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 Seattle/Tacoma Intl (8%) and Las Vegas Harry Reid 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, Rome and Paris.

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 (54% 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 Traverse City, Rapid City, Jacksonville, Los Angeles and Fayetteville. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Los Angeles at $218, while the most expensive was Traverse City, at $365.

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 Edinburgh, Guadalajara, Morelia, Guatemala City and Monterrey. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Monterrey at $195, while the most expensive was Edinburgh, at $2,460.

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 15h 20m, followed by a flight to Seoul at 14h 30m.

Good to know

Low season

January

High season

June

Cheapest flight

$26
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from Chicago O'Hare Airport to Fort Lauderdale

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 $166 round-trip
    2. Marion
      from $192 round-trip
    3. Boston
      from $222 round-trip
    4. Atlanta
      from $230 round-trip
    5. Savannah
      from $231 round-trip
    6. Philadelphia
      from $236 round-trip
    7. Lexington
      from $249 round-trip
    8. Atlantic City
      from $252 round-trip
    9. Charlotte
      from $255 round-trip
    10. Indianapolis
      from $258 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 27% 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 10410 reviews
7.9Comfort
8.0Entertainment
8.2Boarding
8.6Crew
7.4Food
Airline reviews

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

10.0 ExcellentBarb, Jun 2024MSP - JFK
Read more about Delta reviews

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

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

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

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?

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.

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.

It was nice! There was a very unhappy child in front of us and the flight attendant did a great job calming the child. I was impressed.

The plane was not on time for boarding or departure or arrivals.

EVERYTHING WAS WONDERFUL HOSPITALITY THE HELP.THE SEATING FRIENDLY ALWAYS HAVE A GOOD RIDE NOT ONE BAD EXPERIENCE WITH THEM

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

No food not even water offered unless you buy it and no usb in the seat but other than that everything was good

Because our flight from marsh Harbor to Fort Lauderdale was over three hours delayed it caused us to miss our flight in Fort Lauderdale. Because we missed that flight, it cost us nearly $100 apiece for four different travelers which totaled nearly $400. We are seeking a reimbursement for the flight that we missed in Fort Lauderdale Florida.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

Flight was cancelled just 6 days before. No more flights that day, and the following date was sold out. Had to obtain a refund and buy more expensive flights on another airline.

The flight was on time and nice as always for me with spirit but the cabin crew were not good. They left the lights on on a red eye for the entire flight.

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

Book cheap domestic flights from Chicago

Recent round-trip flight deals

9/10Tue
nonstopSpirit Airlines
3h 04mORD-FLL
9/11Wed
nonstopSpirit Airlines
3h 18mFLL-ORD
$50
9/10Tue
nonstopSpirit Airlines
3h 07mORD-FLL
9/11Wed
nonstopSpirit Airlines
3h 18mFLL-ORD
$51
6/25Tue
nonstopFrontier
2h 29mORD-DFW
7/9Tue
nonstopFrontier
2h 34mDFW-ORD
$58
6/25Tue
nonstopFrontier
2h 29mORD-DFW
7/2Tue
nonstopFrontier
2h 23mDFW-ORD
$60
9/4Wed
nonstopAmerican Airlines
2h 15mORD-JFK
9/11Wed
nonstopAmerican Airlines
2h 41mJFK-ORD
$137
9/11Wed
nonstopAmerican Airlines
2h 15mORD-JFK
9/15Sun
nonstopAmerican Airlines
2h 41mJFK-ORD
$153
8/13Tue
nonstopUnited Airlines
4h 39mORD-SEA
8/21Wed
1 stopUnited Airlines
9h 45mSEA-ORD
$154
8/13Tue
nonstopUnited Airlines
4h 38mORD-SEA
8/20Tue
nonstopUnited Airlines
4h 00mSEA-ORD
$166
6/12Wed
nonstopDelta
2h 23mORD-LGA
8/13Tue
nonstopDelta
2h 47mLGA-ORD
$167
7/26Fri
nonstopDelta
2h 09mORD-LGA
7/29Mon
nonstopDelta
2h 47mLGA-ORD
$169

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Recent one-way flight deals

8/28Wed
nonstopSpirit Airlines
3h 10mORD-FLL
$26
6/12Wed
nonstopSpirit Airlines
2h 32mORD-DFW
$30
8/7Wed
nonstopFrontier
2h 39mORD-DFW
$39
8/10Sat
nonstopFrontier
2h 39mORD-DFW
$40
11/2Sat
nonstopAmerican Airlines
2h 18mORD-EWR
$60
7/3Wed
nonstopDelta
2h 09mORD-LGA
$64
9/1Sun
nonstopUnited Airlines
3h 07mORD-FLL
$69
9/11Wed
nonstopDelta
2h 26mORD-JFK
$69
6/25Tue
nonstopUnited Airlines
2h 23mORD-EWR
$85
10/28Mon
nonstopAmerican Airlines
2h 12mORD-JFK
$86

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Last minute flights from Chicago to Anywhere

Last minute flight, train and bus deals

6/7Fri
nonstop
2h 56mORD-MCO
6/11Tue
nonstop
3h 14mMCO-ORD
$113
6/7Fri
nonstop
2h 56mORD-MCO
6/11Tue
multi-stop
19h 29mMCO-ORD
$131
6/7Fri
nonstopSpirit Airlines
3h 20mORD-MIA
6/16Sun
nonstopSpirit Airlines
3h 29mMIA-ORD
$136
6/4Tue
nonstopSpirit Airlines
4h 02mORD-LAS
6/12Wed
nonstopSpirit Airlines
3h 47mLAS-ORD
$140
6/5Wed
multi-stopFrontier
5h 50mORD-MCO
6/12Wed
nonstopFrontier
3h 09mMCO-ORD
$148
6/4Tue
multi-stopFrontier
9h 44mORD-DFW
6/11Tue
nonstopFrontier
2h 23mDFW-ORD
$158
6/7Fri
nonstopUnited Airlines
2h 21mORD-LGA
6/9Sun
nonstopUnited Airlines
2h 35mLGA-ORD
$207
6/7Fri
nonstopAmerican Airlines
2h 04mORD-LGA
6/10Mon
nonstopAmerican Airlines
2h 34mLGA-ORD
$252
6/7Fri
nonstopAmerican Airlines
2h 11mORD-EWR
6/9Sun
nonstopAmerican Airlines
2h 34mEWR-ORD
$252
6/7Fri
nonstopUnited Airlines
2h 20mORD-EWR
6/9Sun
nonstopUnited Airlines
2h 35mEWR-ORD
$317

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Book cheap international flights from Chicago

Recent round-trip flight deals

9/23Mon
nonstopSpirit Airlines
3h 40mORD-CUN
9/28Sat
nonstopSpirit Airlines
4h 01mCUN-ORD
$198
9/9Mon
nonstopSpirit Airlines
3h 40mORD-CUN
9/18Wed
nonstopSpirit Airlines
4h 01mCUN-ORD
$199
9/14Sat
nonstopSpirit Airlines
3h 40mORD-CUN
9/21Sat
nonstopSpirit Airlines
4h 01mCUN-ORD
$201
6/17Mon
multi-stopFrontier
7h 15mMDW-CUN
6/26Wed
multi-stopFrontier
6h 40mCUN-MDW
$293
7/1Mon
multi-stopFrontier
7h 15mMDW-CUN
7/3Wed
multi-stopFrontier
20h 14mCUN-MDW
$295
10/19Sat
multi-stopAmerican Airlines
12h 50mORD-CUN
10/23Wed
nonstopAmerican Airlines
4h 02mCUN-ORD
$335
10/26Sat
multi-stopUnited Airlines
14h 44mORD-CUN
11/2Sat
multi-stopUnited Airlines
14h 25mCUN-ORD
$340
8/3Sat
multi-stopAmerican Airlines
29h 08mORD-CUN
8/10Sat
multi-stopAmerican Airlines
13h 50mCUN-ORD
$358
9/25Wed
multi-stopDelta
11h 45mMDW-CUN
9/28Sat
multi-stopDelta
12h 04mCUN-MDW
$390
9/20Fri
multi-stopDelta
11h 45mMDW-CUN
9/24Tue
multi-stopDelta
13h 23mCUN-MDW
$401

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Recent one-way flight deals

7/9Tue
nonstopSpirit Airlines
3h 31mORD-CUN
$79
7/9Tue
nonstopSpirit Airlines
3h 31mORD-CUN
$87
10/21Mon
multi-stopAmerican Airlines
6h 39mORD-CUN
$92
10/21Mon
nonstopAmerican Airlines
3h 36mORD-CUN
$98
9/3Tue
multi-stopUnited Airlines
7h 17mORD-CUN
$110
8/6Tue
multi-stopUnited Airlines
7h 44mORD-CUN
$115
10/21Mon
multi-stopFrontier
19h 37mMDW-CUN
$122
6/13Thu
multi-stopFrontier
13h 29mMDW-CUN
$127
7/23Tue
multi-stopDelta
9h 27mMDW-CUN
$180
7/23Tue
multi-stopDelta
10h 55mORD-CUN
$180

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Flights from Chicago to Anywhere

Return flight deals:

Anywhere - Chicago

Cabin classes:

$172
$194
$296
$37