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Find deals on flights from Chicago from $38

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 6/12. 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
Fri 6/7
Fri 6/14

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Where can I fly from Chicago?

Prices from CHI, departing Fri 6/7 and returning Fri 6/14

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 (7%) 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 Mexico City, Tokyo and Paris.

What are the most popular countries to fly to from Chicago?

The most popular countries KAYAK users have searched for from Chicago along with the average price for the route clicked by KAYAK users in the last 2 weeks.
Based on KAYAK flight searches, the most countries to fly to from Chicago is United States (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 $227, while the most expensive was Honolulu, at $519.

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 Guadalajara at $196, while the most expensive was Edinburgh, at $1,746.

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

$38
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from Chicago O'Hare Airport to Orlando 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. Marion
      from $154 round-trip
    3. Lafayette
      from $208 round-trip
    4. Bay City
      from $228 round-trip
    5. Islip
      from $230 round-trip
    6. Punta Gorda
      from $248 round-trip
    7. Atlanta
      from $250 round-trip
    8. El Paso
      from $251 round-trip
    9. Ironwood
      from $252 round-trip
    10. Huntsville
      from $256 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 18% 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 10789 reviews
8.2Boarding
8.0Entertainment
7.4Food
7.9Comfort
8.6Crew
Airline reviews

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

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

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.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

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.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

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.

For it to have left on time! Instead of two hours early with zero notice

Flight kept delayed from morning to late afternoon so I had to make other arrangements

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

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 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Book cheap domestic flights from Chicago

Recent round-trip flight deals

6/11Tue
nonstopSpirit Airlines
2h 18mORD-LGA
6/18Tue
nonstopSpirit Airlines
2h 38mLGA-ORD
$75
5/29Wed
1 stopSpirit Airlines
12h 22mORD-LGA
6/1Sat
nonstopSpirit Airlines
2h 37mLGA-ORD
$76
5/21Tue
nonstopFrontier
4h 10mORD-LAS
5/22Wed
nonstopFrontier
3h 46mLAS-ORD
$77
5/22Wed
nonstopFrontier
2h 58mORD-MCO
5/28Tue
nonstopFrontier
3h 09mMCO-ORD
$80
5/29Wed
nonstopDelta
2h 33mORD-JFK
6/1Sat
nonstopDelta
2h 51mJFK-ORD
$122
5/29Wed
nonstopDelta
2h 15mORD-LGA
6/5Wed
nonstopDelta
2h 35mLGA-ORD
$127
5/30Thu
nonstopAmerican Airlines
2h 03mORD-LGA
6/2Sun
nonstopAmerican Airlines
2h 35mLGA-ORD
$148
5/29Wed
1 stopUnited Airlines
4h 02mORD-EWR
6/5Wed
nonstopUnited Airlines
2h 35mEWR-ORD
$152
5/29Wed
nonstopAmerican Airlines
2h 04mORD-EWR
6/3Mon
nonstopAmerican Airlines
2h 40mEWR-ORD
$153
5/21Tue
1 stopUnited Airlines
4h 26mORD-BOS
5/26Sun
nonstopUnited Airlines
2h 50mBOS-ORD
$176

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Recent one-way flight deals

6/12Wed
nonstopSpirit Airlines
2h 29mORD-BOS
$25
6/12Wed
nonstopSpirit Airlines
2h 29mORD-BOS
$26
7/10Wed
nonstopFrontier
2h 58mORD-MCO
$39
8/5Mon
nonstopFrontier
2h 58mORD-MCO
$44
7/9Tue
nonstopAmerican Airlines
2h 38mORD-JFK
$65
7/2Tue
nonstopDelta
2h 09mORD-LGA
$69
7/9Tue
nonstopAmerican Airlines
2h 16mORD-LGA
$70
6/27Thu
nonstopDelta
2h 19mORD-LGA
$85
6/8Sat
nonstopUnited Airlines
2h 21mORD-LGA
$99
5/28Tue
nonstopUnited Airlines
4h 26mORD-LAX
$103

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Last minute flights from Chicago to Anywhere

Last minute flight, train and bus deals

5/13Mon
multi-stopSpirit Airlines
8h 55mORD-FLL
5/14Tue
nonstopSpirit Airlines
3h 13mFLL-ORD
$95
5/13Mon
multi-stopSpirit Airlines
22h 45mORD-FLL
5/15Wed
multi-stopSpirit Airlines
11h 58mFLL-ORD
$109
5/13Mon
nonstopFrontier
2h 56mORD-MCO
5/15Wed
nonstopFrontier
3h 04mMCO-ORD
$119
5/10Fri
nonstopFrontier
2h 56mORD-MCO
5/14Tue
nonstopFrontier
3h 07mMCO-ORD
$126
5/13Mon
nonstopUnited Airlines
2h 21mORD-BOS
5/18Sat
nonstopUnited Airlines
2h 53mBOS-ORD
$211
5/13Mon
multi-stopAmerican Airlines
5h 37mORD-BOS
5/16Thu
nonstopAmerican Airlines
2h 56mBOS-ORD
$227
5/11Sat
nonstopAmerican Airlines
2h 38mORD-MCO
5/14Tue
nonstopAmerican Airlines
3h 01mMCO-ORD
$243
5/11Sat
multi-stopDelta
5h 18mORD-MCO
5/18Sat
multi-stopDelta
7h 12mMCO-ORD
$262
5/11Sat
nonstopDelta
2h 29mORD-BOS
5/14Tue
nonstopDelta
3h 02mBOS-ORD
$283
5/9Thu
nonstopUnited Airlines
2h 12mORD-EWR
6/11Tue
nonstopUnited Airlines
2h 35mEWR-ORD
$308

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Book cheap international flights from Chicago

Recent round-trip flight deals

7/10Wed
nonstopSpirit Airlines
3h 31mORD-CUN
7/17Wed
nonstopSpirit Airlines
4h 12mCUN-ORD
$181
7/10Wed
nonstopSpirit Airlines
3h 31mORD-CUN
7/17Wed
nonstopSpirit Airlines
4h 12mCUN-ORD
$183
5/19Sun
nonstopFrontier
3h 57mORD-CUN
5/23Thu
nonstopFrontier
4h 08mCUN-ORD
$184
5/21Tue
nonstopFrontier
3h 57mORD-CUN
5/23Thu
nonstopFrontier
4h 08mCUN-ORD
$185
5/19Sun
nonstopFrontier
3h 57mORD-CUN
5/24Fri
nonstopFrontier
4h 08mCUN-ORD
$190
7/10Wed
nonstop
3h 31mORD-CUN
7/17Wed
nonstop
4h 03mCUN-ORD
$191
7/15Mon
nonstop
3h 54mORD-CUN
7/17Wed
nonstop
4h 12mCUN-ORD
$196
10/22Tue
multi-stopDelta
6h 48mMDW-CUN
10/29Tue
multi-stopDelta
14h 47mCUN-MDW
$390
6/5Wed
multi-stopDelta
10h 19mMDW-CUN
6/12Wed
multi-stopDelta
12h 12mCUN-MDW
$394
7/23Tue
multi-stopAeromexico
5h 19mMDW-CUN
7/31Wed
multi-stopAeromexico
9h 44mCUN-MDW
$452

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Recent one-way flight deals

5/14Tue
nonstopFrontier
4h 08mORD-CUN
$81
5/29Wed
nonstopFrontier
3h 57mORD-CUN
$86
6/18Tue
nonstopSpirit Airlines
3h 31mORD-CUN
$87
6/3Mon
multi-stopSpirit Airlines
12h 14mORD-CUN
$88
6/25Tue
nonstopSpirit Airlines
3h 31mORD-CUN
$89
5/29Wed
multi-stopAmerican Airlines
6h 46mORD-CUN
$92
5/15Wed
nonstopUnited Airlines
3h 46mORD-CUN
$106
5/15Wed
multi-stopUnited Airlines
8h 00mORD-CUN
$110
5/15Wed
multi-stopDelta
7h 09mMDW-CUN
$180
5/12Sun
multi-stopDelta
12h 42mORD-CUN
$180

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Flights from Chicago to Anywhere

Return flight deals:

Anywhere - Chicago

Cabin classes:

$234
$329
$277
$27