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Find deals on flights from Chicago from $36

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 8/24. 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 6/29
Sat 7/6

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Where can I fly from Chicago?

Prices from CHI, departing Sat 6/29 and returning Sat 7/6

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 (20% 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 Mexico City, Tokyo 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 (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 Shanghai Hongqiao Intl Airport at 14h 30m.

Good to know

Low season

January

High season

June

Cheapest flight

$36
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 24% 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. Burlington
      from $181 round-trip
    2. Quincy
      from $202 round-trip
    3. Atlanta
      from $232 round-trip
    4. Boston
      from $233 round-trip
    5. Punta Gorda
      from $241 round-trip
    6. Ironwood
      from $248 round-trip
    7. Philadelphia
      from $250 round-trip
    8. Myrtle Beach
      from $254 round-trip
    9. Atlantic City
      from $254 round-trip
    10. State College
      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 24% 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 10457 reviews
8.6Crew
7.9Comfort
8.0Entertainment
8.2Boarding
7.4Food
Airline reviews

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.

10.0 ExcellentAnonymous, May 2024MSP - YVR
Read more about Delta reviews

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

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

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?

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

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.

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!

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

This recognisable no-frills airline gets me from point-A to point-B. I was able to get to Chicago without stress. The checked baggage collection and reclaim could be improved.

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.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

Book cheap domestic flights from Chicago

Recent round-trip flight deals

8/27Tue
nonstopSpirit Airlines
2h 18mORD-BOS
8/28Wed
nonstopSpirit Airlines
2h 33mBOS-ORD
$33
9/10Tue
nonstopSpirit Airlines
2h 11mORD-LGA
9/11Wed
nonstopSpirit Airlines
2h 39mLGA-ORD
$40
6/12Wed
nonstopFrontier
2h 56mORD-MCO
6/14Fri
nonstopFrontier
3h 09mMCO-ORD
$95
10/15Tue
nonstopFrontier
2h 58mORD-MCO
10/22Tue
nonstopFrontier
3h 00mMCO-ORD
$98
8/28Wed
nonstopDelta
2h 14mORD-LGA
8/31Sat
nonstopDelta
2h 40mLGA-ORD
$133
8/27Tue
nonstopDelta
4h 25mORD-SEA
8/31Sat
nonstopDelta
3h 56mSEA-ORD
$149
6/11Tue
nonstopAmerican Airlines
2h 26mORD-JFK
6/26Wed
nonstopAmerican Airlines
2h 57mJFK-ORD
$154
6/25Tue
nonstopAmerican Airlines
2h 26mORD-JFK
6/26Wed
nonstopAmerican Airlines
2h 57mJFK-ORD
$157
8/17Sat
nonstopUnited Airlines
4h 40mORD-SEA
8/24Sat
nonstopUnited Airlines
4h 00mSEA-ORD
$166
6/28Fri
nonstopUnited Airlines
2h 20mORD-EWR
7/1Mon
1 stopUnited Airlines
4h 10mEWR-ORD
$179

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Recent one-way flight deals

8/24Sat
nonstopSpirit Airlines
2h 12mORD-LGA
$23
9/10Tue
nonstopSpirit Airlines
2h 18mORD-BOS
$23
8/28Wed
1 stopFrontier
6h 06mORD-MIA
$48
6/18Tue
nonstopFrontier
2h 52mORD-MCO
$49
9/9Mon
nonstopAmerican Airlines
2h 24mORD-EWR
$60
11/14Thu
nonstopAmerican Airlines
2h 18mORD-EWR
$61
8/28Wed
nonstopDelta
2h 09mORD-LGA
$64
9/1Sun
nonstopDelta
4h 25mORD-SEA
$75
7/20Sat
nonstopUnited Airlines
2h 21mORD-LGA
$83
7/1Mon
nonstopUnited Airlines
4h 01mORD-LAS
$89

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Last minute flights from Chicago to Anywhere

Last minute flight, train and bus deals

6/4Tue
multi-stopSpirit Airlines
11h 01mORD-BOS
6/5Wed
multi-stopSpirit Airlines
12h 30mBOS-ORD
$70
6/4Tue
nonstopSpirit Airlines
3h 17mORD-MIA
6/6Thu
nonstopSpirit Airlines
3h 29mMIA-ORD
$83
6/4Tue
multi-stopFrontier
6h 52mORD-MIA
6/5Wed
multi-stopFrontier
14h 18mMIA-ORD
$100
6/4Tue
multi-stopFrontier
6h 15mORD-MIA
6/8Sat
multi-stopFrontier
9h 00mMIA-ORD
$104
6/4Tue
nonstopAmerican Airlines
2h 26mORD-BOS
6/5Wed
nonstopAmerican Airlines
3h 06mBOS-ORD
$167
6/4Tue
multi-stopDelta
5h 05mORD-BOS
6/21Fri
nonstopDelta
2h 57mBOS-ORD
$237
6/3Mon
multi-stopDelta
5h 05mORD-BOS
6/5Wed
nonstopDelta
3h 02mBOS-ORD
$243
6/4Tue
multi-stopAmerican Airlines
4h 03mORD-JFK
6/13Thu
nonstopAmerican Airlines
2h 51mJFK-ORD
$247
6/4Tue
nonstopUnited Airlines
2h 20mORD-EWR
7/10Wed
nonstopUnited Airlines
2h 37mEWR-ORD
$282
6/4Tue
nonstopUnited Airlines
2h 20mORD-EWR
6/12Wed
nonstopUnited Airlines
2h 35mEWR-ORD
$304

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Book cheap international flights from Chicago

Recent round-trip flight deals

9/9Mon
nonstopFrontier
3h 54mORD-CUN
9/18Wed
nonstopFrontier
4h 03mCUN-ORD
$185
10/8Tue
nonstopFrontier
3h 54mORD-CUN
10/16Wed
nonstopFrontier
4h 03mCUN-ORD
$188
9/5Thu
nonstopFrontier
3h 54mORD-CUN
9/10Tue
nonstopFrontier
4h 03mCUN-ORD
$191
9/25Wed
nonstopFrontier
3h 54mORD-CUN
10/3Thu
nonstopFrontier
4h 03mCUN-ORD
$192
8/24Sat
nonstopSpirit Airlines
3h 32mORD-CUN
8/27Tue
nonstopSpirit Airlines
4h 00mCUN-ORD
$199
7/14Sun
nonstopSpirit Airlines
3h 31mORD-CUN
7/17Wed
nonstopSpirit Airlines
4h 12mCUN-ORD
$200
9/26Thu
nonstopVolaris
3h 54mORD-CUN
9/30Mon
nonstopVolaris
4h 03mCUN-ORD
$338
10/8Tue
multi-stopUnited Airlines
11h 45mORD-CUN
10/15Tue
multi-stopUnited Airlines
14h 51mCUN-ORD
$340
8/24Sat
multi-stopDelta
9h 27mMDW-CUN
8/29Thu
multi-stopDelta
13h 46mCUN-MDW
$390
8/26Mon
multi-stopDelta
8h 07mMDW-CUN
8/31Sat
multi-stopDelta
9h 04mCUN-MDW
$394

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Recent one-way flight deals

7/9Tue
nonstopSpirit Airlines
3h 31mORD-CUN
$79
9/11Wed
nonstopFrontier
3h 54mORD-CUN
$81
7/30Tue
multi-stopUnited Airlines
7h 44mORD-CUN
$115
6/4Tue
multi-stopUnited Airlines
6h 35mORD-CUN
$134
6/4Tue
multi-stopAmerican Airlines
6h 20mORD-CUN
$135
7/3Wed
multi-stopAmerican Airlines
16h 49mORD-CUN
$160
6/5Wed
multi-stopDelta
10h 19mMDW-CUN
$180
6/5Wed
multi-stopDelta
10h 19mMDW-CUN
$192
6/27Thu
multi-stopVolaris
16h 38mORD-CUN
$267
9/2Mon
multi-stopVolaris
14h 21mMDW-CUN
$324

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Flights from Chicago to Anywhere

Return flight deals:

Anywhere - Chicago

Cabin classes:

$172
$194
$296
$37