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$28 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 9/12. 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 7/13
Sat 7/20

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Where can I fly from Chicago?

Prices from CHI, departing Sat 7/13 and returning Sat 7/20

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 (15% of total searches). The next most popular destinations are Seattle/Tacoma Intl (8%) and Los Angeles (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 Tokyo, Paris 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 El Paso. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Los Angeles at $226, while the most expensive was El Paso, at $380.

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, Edinburgh, Puerto Vallarta, Guadalajara and Morelia. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Morelia at $172, while the most expensive was Edinburgh, at $1,914.

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 05m, followed by a flight to Shanghai Hongqiao Intl Airport at 14h 30m.

Good to know

Low season

January

High season

March

Cheapest flight

$28
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 14% 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. Mason City
      from $211 round-trip
    2. Boston
      from $234 round-trip
    3. Atlanta
      from $252 round-trip
    4. Lafayette
      from $253 round-trip
    5. Punta Gorda
      from $254 round-trip
    6. Trenton
      from $256 round-trip
    7. Tulsa
      from $258 round-trip
    8. Huntsville
      from $259 round-trip
    9. Grand Rapids
      from $263 round-trip
    10. Philadelphia
      from $264 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 12% 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 10000 reviews
7.4Food
7.9Comfort
8.2Boarding
8.6Crew
8.0Entertainment
Airline reviews

It was very cold because the air conditioner was on high power, and my son got sick.

4.0 OkayAnonymous, Jun 2024ORD - SEA
Read more about Delta reviews

It was very cold because the air conditioner was on high power, and my son got sick.

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

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

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.

Poor response to delay, getting on plane, off plane and back on again

My flight was uncomfortable and crammed. There were no pockets to store things, I couldn’t move my seat back slightly. Beverages including soda cost extra. My husband flew on another spirit airline flight, which was delayed a total of 48 hours, only to be canceled.

Two delays in less than 24hrs. They need to improve everything and restructure the whole company.

Terrible leg room, seats don’t recline, delayed flight, and even water isn’t free onboard

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

I did not enjoy the trip home on Frontier for several reasons: there is too much cost besides the flight, which was more than I would normally pay, then having to pay for luggage, and carry-on, seat (if you want to reserve when booking) then you must pay over $3 for a can of soda, and $4 for a snack. A cup of water is free.

Did not realize seats did not recline. Best to travel in an exit row... No question

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

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

Book cheap domestic flights from Chicago

Recent round-trip flight deals

8/20Tue
nonstopFrontier
2h 37mORD-DFW
8/21Wed
nonstopFrontier
2h 39mDFW-ORD
$48
9/10Tue
nonstopSpirit Airlines
3h 07mORD-FLL
9/11Wed
nonstopSpirit Airlines
3h 17mFLL-ORD
$50
9/9Mon
nonstopAlaska Airlines
4h 33mORD-SEA
9/9Mon
nonstopAlaska Airlines
3h 53mSEA-ORD
$91
12/10Tue
nonstopUnited Airlines
2h 10mORD-LGA
12/17Tue
nonstopUnited Airlines
2h 25mLGA-ORD
$97
9/18Wed
nonstopAlaska Airlines
4h 34mORD-SEA
9/24Tue
nonstopAlaska Airlines
3h 53mSEA-ORD
$97
8/23Fri
nonstopDelta
2h 19mORD-LGA
8/28Wed
nonstopDelta
2h 54mLGA-ORD
$101
8/24Sat
nonstopUnited Airlines
4h 33mORD-SEA
9/4Wed
1 stopUnited Airlines
9h 45mSEA-ORD
$119
9/11Wed
nonstopDelta
4h 33mORD-SEA
9/18Wed
nonstopDelta
4h 05mSEA-ORD
$123
12/4Wed
nonstopAmerican Airlines
2h 47mORD-DFW
12/8Sun
nonstopAmerican Airlines
2h 26mDFW-ORD
$125
8/24Sat
nonstopAmerican Airlines
2h 30mORD-JFK
9/7Sat
nonstopAmerican Airlines
2h 41mJFK-ORD
$144

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Recent one-way flight deals

9/12Thu
nonstopFrontier
4h 18mORD-LAS
$23
9/10Tue
nonstopSpirit Airlines
3h 10mORD-FLL
$24
9/1Sun
nonstopDelta
4h 25mORD-SEA
$49
9/9Mon
nonstopDelta
2h 20mORD-LGA
$51
10/18Fri
nonstopAmerican Airlines
2h 33mORD-JFK
$52
8/12Mon
nonstopUnited Airlines
3h 12mORD-FLL
$63
8/22Thu
nonstopAmerican Airlines
2h 39mORD-MCO
$63
7/9Tue
nonstopUnited Airlines
2h 21mORD-EWR
$69
8/13Tue
nonstopAlaska Airlines
4h 37mORD-SFO
$69
8/19Mon
nonstopAlaska Airlines
4h 37mORD-SFO
$73

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Last minute flights from Chicago to Anywhere

Last minute flight, train and bus deals

6/18Tue
nonstopFrontier
2h 29mORD-DFW
6/25Tue
nonstopFrontier
2h 23mDFW-ORD
$120
6/18Tue
nonstopFrontier
4h 09mORD-LAS
7/9Tue
nonstopFrontier
3h 47mLAS-ORD
$134
6/18Tue
multi-stopSpirit Airlines
11h 33mORD-MCO
6/25Tue
nonstopSpirit Airlines
3h 14mMCO-ORD
$147
6/18Tue
multi-stopSpirit Airlines
14h 03mORD-EWR
7/2Tue
multi-stopSpirit Airlines
10h 05mEWR-ORD
$148
6/18Tue
nonstopAmerican Airlines
2h 11mORD-EWR
7/2Tue
nonstopAmerican Airlines
2h 37mEWR-ORD
$188
6/18Tue
nonstopDelta
2h 15mORD-LGA
6/21Fri
nonstopDelta
2h 35mLGA-ORD
$207
6/18Tue
nonstopAmerican Airlines
2h 26mORD-JFK
6/25Tue
multi-stopAmerican Airlines
4h 20mJFK-ORD
$232
6/18Tue
nonstopDelta
2h 21mORD-JFK
6/19Wed
nonstopDelta
2h 58mJFK-ORD
$247
6/18Tue
multi-stopUnited Airlines
5h 54mORD-EWR
6/25Tue
nonstopUnited Airlines
2h 35mEWR-ORD
$287
6/15Sat
nonstopUnited Airlines
2h 23mORD-EWR
7/2Tue
nonstopUnited Airlines
2h 35mEWR-ORD
$317

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Book cheap international flights from Chicago

Recent round-trip flight deals

9/11Wed
nonstopFrontier
3h 54mORD-CUN
9/18Wed
nonstopFrontier
4h 03mCUN-ORD
$185
7/9Tue
nonstopFrontier
3h 49mORD-CUN
7/11Thu
nonstopFrontier
4h 04mCUN-ORD
$186
7/9Tue
nonstopSpirit Airlines
3h 31mORD-CUN
7/17Wed
nonstopSpirit Airlines
4h 12mCUN-ORD
$197
7/14Sun
nonstopSpirit Airlines
3h 31mORD-CUN
7/17Wed
nonstopSpirit Airlines
4h 12mCUN-ORD
$199
9/6Fri
multi-stopAmerican Airlines
10h 59mORD-CUN
9/13Fri
multi-stopAmerican Airlines
13h 09mCUN-ORD
$202
10/15Tue
multi-stopAmerican Airlines
9h 29mORD-CUN
10/22Tue
nonstopAmerican Airlines
4h 02mCUN-ORD
$225
9/17Tue
multi-stopDelta
7h 08mMDW-CUN
9/24Tue
multi-stopDelta
12h 02mCUN-MDW
$400
12/4Wed
multi-stopAeromexico
6h 48mMDW-CUN
12/13Fri
multi-stopAeromexico
6h 56mCUN-MDW
$411
9/20Fri
multi-stopDelta
11h 45mMDW-CUN
9/24Tue
multi-stopDelta
12h 02mCUN-MDW
$443
10/15Tue
multi-stopAeromexico
6h 48mMDW-CUN
10/22Tue
multi-stopAeromexico
9h 44mCUN-MDW
$455

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Recent one-way flight deals

7/9Tue
nonstopFrontier
3h 49mORD-CUN
$78
7/9Tue
nonstopFrontier
3h 49mORD-CUN
$80
7/16Tue
nonstopSpirit Airlines
3h 31mORD-CUN
$86
9/6Fri
nonstopSpirit Airlines
3h 31mORD-CUN
$87
8/5Mon
nonstopAmerican Airlines
3h 55mORD-CUN
$98
8/18Sun
nonstopUnited Airlines
3h 46mORD-CUN
$105
9/12Thu
multi-stopAmerican Airlines
12h 34mORD-CUN
$114
8/16Fri
nonstopUnited Airlines
3h 46mORD-CUN
$117
10/18Fri
multi-stopDelta
10h 23mORD-CUN
$196
7/9Tue
multi-stopDelta
10h 22mMDW-CUN
$229

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Flights from Chicago to Anywhere

Return flight deals:

Anywhere - Chicago

Cabin classes:

$172
$194
$310
$37