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Find deals on flights from Chicago from $29

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 7/23. 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 6/22
Sat 6/29

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Where can I fly from Chicago?

Prices from CHI, departing Sat 6/22 and returning Sat 6/29

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 (17% of total searches). The next most popular destinations are Las Vegas Harry Reid Intl (8%) and Seattle/Tacoma Intl (7%).

What are the most popular international flights out of Chicago?

The international destinations KAYAK users have most searched for when searching for flights from Chicago.
There are many international destinations you can fly to from Chicago. The most popular international destinations among KAYAK users are Rome, 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 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 (5%) 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 El Paso. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Los Angeles at $217, while the most expensive was El Paso, at $394.

Which international cities can I fly to direct from Chicago?

There are many international destinations you can fly to non-stop from Chicago. The most popular international destinations from KAYAK users are Paris, Guadalajara, Morelia, León and Guatemala City. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Guadalajara at $194, while the most expensive was Paris, at $890.

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

March

Cheapest flight

$29
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 13% 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. Manistee
      from $173 round-trip
    2. Islip
      from $243 round-trip
    3. Atlanta
      from $255 round-trip
    4. Boston
      from $257 round-trip
    5. Charlotte
      from $258 round-trip
    6. San Diego
      from $260 round-trip
    7. Philadelphia
      from $261 round-trip
    8. Fort Myers
      from $263 round-trip
    9. Boise
      from $269 round-trip
    10. Trenton
      from $270 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 23% 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 10561 reviews
7.9Comfort
8.0Entertainment
8.6Crew
8.2Boarding
7.4Food
Airline reviews

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

2.0 MediocreNairan, May 2024JFK - FLL
Read more about Delta reviews

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.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

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!

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

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.

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.

The crew was the best and very accommodating I know you don't offer any complimentary items but water and coffee will not break the bank !!

My flight was cancelled!!! I had to spend 200.00 on another flight!!

The whole day was a nightmare. Flight extremely late. Boarding was a mess of a nightmare.

When we landed, they kept us on the plane for almost 25 minutes. Could do better.

worst trip ever Spirit lost our Baggs which were never put on the plane in Atlanta. 24 hours ago they are telling me now that the bags are still missing.

Never been on this flight as i had missed it due to delayed connecting flight

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

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 .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

Book cheap domestic flights from Chicago

Recent round-trip flight deals

6/5Wed
nonstopSpirit Airlines
3h 13mORD-FLL
6/11Tue
nonstopSpirit Airlines
3h 22mFLL-ORD
$39
6/5Wed
nonstopSpirit Airlines
3h 13mORD-FLL
6/11Tue
nonstopSpirit Airlines
3h 22mFLL-ORD
$40
6/4Tue
nonstopFrontier
2h 31mORD-DFW
6/5Wed
nonstopFrontier
2h 23mDFW-ORD
$76
8/13Tue
nonstopFrontier
2h 37mORD-DFW
8/20Tue
nonstopFrontier
2h 41mDFW-ORD
$78
7/17Wed
nonstopDelta
2h 14mORD-LGA
7/20Sat
nonstopDelta
2h 59mLGA-ORD
$147
6/5Wed
nonstopUnited Airlines
2h 20mORD-EWR
6/7Fri
nonstopUnited Airlines
2h 35mEWR-ORD
$157
7/16Tue
nonstopAmerican Airlines
2h 38mORD-JFK
7/23Tue
nonstopAmerican Airlines
2h 58mJFK-ORD
$157
6/11Tue
nonstopUnited Airlines
2h 20mORD-EWR
6/18Tue
nonstopUnited Airlines
2h 35mEWR-ORD
$161
6/11Tue
nonstopDelta
2h 09mORD-LGA
6/18Tue
nonstopDelta
2h 35mLGA-ORD
$167
8/16Fri
nonstopAmerican Airlines
2h 05mORD-LGA
8/19Mon
nonstopAmerican Airlines
2h 41mLGA-ORD
$169

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Recent one-way flight deals

7/23Tue
nonstopSpirit Airlines
2h 07mORD-LGA
$23
6/4Tue
nonstopSpirit Airlines
2h 29mORD-DFW
$25
6/26Wed
nonstopFrontier
2h 29mORD-DFW
$34
6/4Tue
nonstopFrontier
2h 31mORD-DFW
$39
6/11Tue
nonstopAmerican Airlines
2h 26mORD-JFK
$59
6/19Wed
nonstopDelta
2h 09mORD-LGA
$64
7/10Wed
nonstopAmerican Airlines
2h 38mORD-JFK
$65
7/23Tue
nonstopDelta
2h 41mORD-JFK
$74
8/1Thu
1 stopUnited Airlines
4h 13mORD-LGA
$94
5/29Wed
nonstopUnited Airlines
2h 33mORD-DFW
$100

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Last minute flights from Chicago to Anywhere

Last minute flight, train and bus deals

5/28Tue
multi-stopSpirit Airlines
7h 02mORD-MCO
6/5Wed
nonstopSpirit Airlines
3h 14mMCO-ORD
$96
5/28Tue
nonstopSpirit Airlines
2h 11mORD-LGA
5/29Wed
multi-stopSpirit Airlines
11h 29mLGA-ORD
$107
5/28Tue
nonstopFrontier
2h 31mORD-DFW
6/4Tue
nonstopFrontier
2h 45mDFW-ORD
$142
5/28Tue
nonstopFrontier
4h 10mORD-LAS
6/1Sat
nonstopFrontier
3h 46mLAS-ORD
$143
5/28Tue
nonstopAmerican Airlines
2h 12mORD-EWR
6/12Wed
nonstopAmerican Airlines
2h 40mEWR-ORD
$223
5/28Tue
nonstopUnited Airlines
2h 20mORD-EWR
6/4Tue
nonstopUnited Airlines
2h 35mEWR-ORD
$228
5/28Tue
nonstopUnited Airlines
2h 20mORD-EWR
5/29Wed
nonstopUnited Airlines
2h 35mEWR-ORD
$236
5/28Tue
nonstopAmerican Airlines
2h 12mORD-EWR
6/4Tue
nonstopAmerican Airlines
2h 40mEWR-ORD
$242
5/28Tue
nonstopDelta
2h 17mORD-LGA
6/4Tue
nonstopDelta
2h 49mLGA-ORD
$262
5/28Tue
nonstopDelta
2h 14mORD-LGA
5/30Thu
nonstopDelta
2h 35mLGA-ORD
$317

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Book cheap international flights from Chicago

Recent round-trip flight deals

8/14Wed
nonstopSpirit Airlines
3h 32mORD-CUN
8/21Wed
nonstopSpirit Airlines
4h 00mCUN-ORD
$179
8/20Tue
nonstopFrontier
3h 54mORD-CUN
8/23Fri
nonstopFrontier
4h 03mCUN-ORD
$185
8/19Mon
nonstopFrontier
3h 54mORD-CUN
8/24Sat
nonstopFrontier
4h 03mCUN-ORD
$186
8/14Wed
nonstopFrontier
3h 54mORD-CUN
8/21Wed
nonstopFrontier
4h 03mCUN-ORD
$193
7/10Wed
nonstopSpirit Airlines
3h 31mORD-CUN
7/16Tue
nonstopSpirit Airlines
4h 12mCUN-ORD
$197
7/9Tue
nonstopSpirit Airlines
3h 31mORD-CUN
7/16Tue
nonstopSpirit Airlines
4h 12mCUN-ORD
$198
5/29Wed
multi-stopAmerican Airlines
6h 20mORD-CUN
6/4Tue
nonstopAmerican Airlines
4h 01mCUN-ORD
$350
8/10Sat
multi-stopDelta
5h 07mMDW-CUN
8/20Tue
multi-stopDelta
11h 57mCUN-MDW
$390
7/13Sat
multi-stopDelta
13h 55mMDW-CUN
7/17Wed
multi-stopDelta
13h 46mCUN-MDW
$401
7/29Mon
multi-stopAeromexico
7h 00mMDW-CUN
8/2Fri
multi-stopAeromexico
13h 46mCUN-MDW
$402

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Recent one-way flight deals

7/9Tue
nonstopSpirit Airlines
3h 31mORD-CUN
$79
5/28Tue
nonstopFrontier
3h 57mORD-CUN
$81
8/24Sat
nonstopFrontier
3h 54mORD-CUN
$82
8/13Tue
nonstopFrontier
3h 54mORD-CUN
$83
5/29Wed
multi-stopUnited Airlines
8h 37mORD-CUN
$115
9/24Tue
multi-stopAmerican Airlines
6h 39mORD-CUN
$134
5/29Wed
multi-stopAmerican Airlines
9h 17mORD-CUN
$135
5/28Tue
multi-stopBritish Airways
14h 43mORD-CUN
$158
6/4Tue
multi-stopDelta
10h 19mMDW-CUN
$180
6/4Tue
multi-stopDelta
11h 06mORD-CUN
$180

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Flights from Chicago to Anywhere

Return flight deals:

Anywhere - Chicago

Cabin classes:

$172
$277
$277
$27