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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 9/18. 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 6/15
Sat 6/22

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Where can I fly from Chicago?

Prices from CHI, departing Sat 6/15 and returning Sat 6/22

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 (19% of total searches). The next most popular destinations are Seattle/Tacoma Intl (6%) and Las Vegas Harry Reid Intl (6%).

What are the most popular international flights out of Chicago?

The international destinations KAYAK users have most searched for when searching for flights from Chicago.
There are many international destinations you can fly to from Chicago. The most popular international destinations among KAYAK users are 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 (53% 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 Rapid City, Jacksonville, Los Angeles, Honolulu and Fayetteville. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Los Angeles at $222, while the most expensive was Honolulu, at $540.

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, Guadalajara, Morelia and León. 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 Edinburgh, at $1,791.

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 14% 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. Owensboro
      from $142 round-trip
    2. Muskegon
      from $182 round-trip
    3. Punta Gorda
      from $202 round-trip
    4. Manistee
      from $210 round-trip
    5. Burlington
      from $219 round-trip
    6. Lafayette
      from $223 round-trip
    7. Islip
      from $227 round-trip
    8. Charleston
      from $239 round-trip
    9. Worcester
      from $247 round-trip
    10. Lewiston
      from $260 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 10673 reviews
7.9Comfort
8.2Boarding
7.4Food
8.0Entertainment
8.6Crew
Airline reviews

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

4.0 OkayReginald, May 2024MCI - LGA
Read more about Delta reviews

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

The plane was FREEZING SEATS UNCOMFORTABLE Otherwise smooth Thank you

Boarding was chaotic. I didn’t finish dinner because I went to bed early. Breakfast omelet was overcooked and tasteless but croissant was better than usual. Plane was dirty—crumbs in every seam and lavatory was poorly maintained (paint peeling, etc.) and toilet paper had not been refreshed before takeoff. No cubby for storage in first and seat was narrow.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

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

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

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.

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

Missed our departing flight due to poor baggage drop staff. At the airport with 2 & 1/2 hours to spare and waited in bag check in until 15 minutes prior to gates closing before baggage staff asked us to move to the front of the line. We weren’t the only passengers that missed the flight. Poor organizational operations by Spirit staff. Otherwise , the return trip was fine.

My experience with Spirit was perfect. Did not expect it to be this good

Worst airline experience ever. Lost my IPad going thru security. Charged for my dog carriage at the gate not at ticket counter. Gave away my seat 6D. Expressed I wanted my seat back after charging me 99 for dog carriage. Should have thrown it out. Had a 16 yr old Yorkie heading to Boston after being a snowbird. Seats small. Very bad experience. Still don’t have my IPad. Horrible

My mother was HARASSED AND ACCOSTED by the gate agent for her bag. I pre purchased the bag fee and the gate agent made my 78 year old mother board, deplane, re pay for her bag fee and board again. The gate agent made my mother pick up her own bag and REFUSED to help her, she is an older woman who wasn’t bothering anyone on a flight that had maybe 30’total passengers. I am going to sue this airlines for their HORRIBLE customer service and treatment of my mother, and all this occurred the day after Mother’s Day!!!

The boarding gate was moved so many times that I missed my flight. No attendants would help me. The wrong gate was even on my boarding pass. I had to repurchase everything. I’ll never fly again. Really a terrible day as I had planned to see a former student who is dying in Louisville Never ever will I forget that day. Your airline is totally uncaring.

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

Hated it I would not use Kayak or Spirit ever again.

They stuck us with multiple extra fees. I will never fly spirit again

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.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Book cheap domestic flights from Chicago

Recent round-trip flight deals

5/28Tue
nonstopSpirit Airlines
3h 05mORD-FLL
6/4Tue
nonstopSpirit Airlines
3h 10mFLL-ORD
$40
5/29Wed
nonstopSpirit Airlines
2h 09mORD-LGA
6/4Tue
nonstopSpirit Airlines
2h 39mLGA-ORD
$43
6/5Wed
nonstopFrontier
2h 57mORD-DEN
6/8Sat
nonstopFrontier
2h 35mDEN-ORD
$57
6/1Sat
nonstopFrontier
2h 49mORD-DEN
6/4Tue
nonstopFrontier
2h 38mDEN-ORD
$58
5/31Fri
nonstopUnited Airlines
2h 21mORD-LGA
6/3Mon
nonstopUnited Airlines
2h 35mLGA-ORD
$117
7/9Tue
nonstopUnited Airlines
2h 37mORD-DEN
7/16Tue
nonstopUnited Airlines
2h 31mDEN-ORD
$139
6/26Wed
nonstopDelta
2h 19mORD-LGA
6/30Sun
nonstopDelta
2h 45mLGA-ORD
$148
9/18Wed
nonstopAmerican Airlines
4h 46mORD-SEA
9/24Tue
nonstopAmerican Airlines
4h 00mSEA-ORD
$150
9/18Wed
nonstopAmerican Airlines
4h 46mORD-SEA
9/24Tue
nonstopAmerican Airlines
4h 00mSEA-ORD
$151
7/2Tue
nonstopDelta
2h 34mORD-JFK
7/13Sat
nonstopDelta
2h 45mJFK-ORD
$152

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Recent one-way flight deals

9/18Wed
nonstopSpirit Airlines
2h 11mORD-LGA
$29
6/25Tue
nonstopSpirit Airlines
3h 07mORD-FLL
$29
6/15Sat
nonstopFrontier
2h 54mORD-DEN
$29
6/29Sat
nonstopFrontier
2h 54mORD-DEN
$30
5/31Fri
nonstopUnited Airlines
2h 21mORD-LGA
$59
5/29Wed
nonstopDelta
2h 33mORD-JFK
$59
6/18Tue
nonstopDelta
2h 23mORD-LGA
$64
7/23Tue
nonstopAmerican Airlines
2h 38mORD-JFK
$65
10/9Wed
nonstopAmerican Airlines
4h 46mORD-SEA
$76
7/13Sat
nonstopUnited Airlines
2h 21mORD-LGA
$83

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Last minute flights from Chicago to Anywhere

Last minute flight, train and bus deals

5/21Tue
nonstop
2h 49mORD-MCO
5/29Wed
nonstop
3h 09mMCO-ORD
$73
5/21Tue
nonstopFrontier
4h 10mORD-LAS
6/4Tue
nonstopFrontier
3h 46mLAS-ORD
$81
5/21Tue
nonstopSpirit Airlines
4h 02mORD-LAS
5/24Fri
nonstopSpirit Airlines
3h 41mLAS-ORD
$94
5/21Tue
multi-stopSpirit Airlines
5h 42mORD-FLL
5/22Wed
multi-stopSpirit Airlines
9h 48mFLL-ORD
$95
5/21Tue
nonstopAmerican Airlines
2h 04mORD-LGA
5/21Tue
nonstopAmerican Airlines
2h 43mLGA-ORD
$227
5/18Sat
multi-stopDelta
4h 59mORD-DEN
5/31Fri
multi-stopDelta
7h 00mDEN-ORD
$254
5/18Sat
multi-stopDelta
5h 49mORD-MCO
5/23Thu
multi-stopDelta
4h 57mMCO-ORD
$262
5/20Mon
multi-stopAmerican Airlines
6h 56mORD-JFK
5/29Wed
nonstopAmerican Airlines
3h 02mJFK-ORD
$280
5/18Sat
nonstopUnited Airlines
2h 48mORD-DEN
5/18Sat
nonstopUnited Airlines
2h 26mDEN-ORD
$281
5/21Tue
nonstopUnited Airlines
4h 46mORD-SFO
5/28Tue
nonstopUnited Airlines
4h 20mSFO-ORD
$291

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Book cheap international flights from Chicago

Recent round-trip flight deals

9/16Mon
nonstopFrontier
3h 54mORD-CUN
9/27Fri
nonstopFrontier
4h 03mCUN-ORD
$185
8/14Wed
nonstopFrontier
3h 54mORD-CUN
8/23Fri
nonstopFrontier
4h 03mCUN-ORD
$188
8/24Sat
nonstopFrontier
3h 54mORD-CUN
8/29Thu
nonstopFrontier
4h 03mCUN-ORD
$189
7/14Sun
nonstopSpirit Airlines
3h 31mORD-CUN
7/19Fri
nonstopSpirit Airlines
4h 12mCUN-ORD
$192
7/17Wed
nonstopSpirit Airlines
3h 31mORD-CUN
7/31Wed
nonstopSpirit Airlines
4h 12mCUN-ORD
$201
9/1Sun
multi-stopAmerican Airlines
7h 45mORD-CUN
9/6Fri
multi-stopAmerican Airlines
10h 30mCUN-ORD
$298
9/16Mon
multi-stopAmerican Airlines
14h 45mORD-CUN
9/27Fri
multi-stopAmerican Airlines
6h 41mCUN-ORD
$341
9/13Fri
multi-stopDelta
6h 48mMDW-CUN
9/25Wed
multi-stopDelta
9h 19mCUN-MDW
$390
9/14Sat
multi-stopDelta
10h 18mMDW-CUN
9/21Sat
multi-stopDelta
12h 44mCUN-MDW
$394
8/13Tue
multi-stopAeromexico
5h 07mMDW-CUN
8/14Wed
multi-stopAeromexico
13h 32mCUN-MDW
$467

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Recent one-way flight deals

7/16Tue
nonstopSpirit Airlines
3h 31mORD-CUN
$79
8/20Tue
nonstopFrontier
3h 54mORD-CUN
$81
8/14Wed
multi-stopUnited Airlines
7h 12mORD-CUN
$110
5/21Tue
multi-stopUnited Airlines
8h 20mORD-CUN
$115
8/14Wed
multi-stopAmerican Airlines
9h 45mORD-CUN
$135
6/5Wed
multi-stopAmerican Airlines
8h 33mORD-CUN
$175
8/13Tue
multi-stopDelta
9h 22mORD-CUN
$176
5/21Tue
multi-stopDelta
10h 19mMDW-CUN
$180
10/6Sun
multi-stopVolaris
17h 33mORD-CUN
$273
6/19Wed
multi-stopVolaris
24h 13mMDW-CUN
$398

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Flights from Chicago to Anywhere

Return flight deals:

Anywhere - Chicago

Cabin classes:

$172
$329
$277
$27