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Find deals on flights from Chicago from C$ 100

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Anywhere departing on 22/5. 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 8/6
Sat 15/6

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Where can I fly from Chicago?

Prices from CHI, departing Sat 6/8 and returning Sat 6/15

Good to know

Low season

January

High season

March

Cheapest flight

C$ 100
Best time to beat the crowds (18% less expensive on average)
Most popular time to fly (1% more expensive on average)
Flight from Chicago O'Hare Airport to Toronto Pearson 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.

  • 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 8% 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.
8.1
EmiratesOverall score based on 3988 reviews
8.2Boarding
8.3Crew
8.1Comfort
7.9Food
8.3Entertainment
Airline reviews

we bought trip insurance from you and could not use it. 'underrated' only return 50 % of trip cost. my doctor told me i have stage 4 cancer and that I might not live till the end of the month..

2.0 MediocreAnonymous, May 2024EWR - ATH
Read more about Emirates reviews

we bought trip insurance from you and could not use it. 'underrated' only return 50 % of trip cost. my doctor told me i have stage 4 cancer and that I might not live till the end of the month..

Flight got canceled without any prior information and it caused lot of trouble

Staff were friendly, and provided great service. The food was plentiful and delicious. Food could have been hotter.

I was traveling business purposes and I only had one carry on and a personal computer back pack . My carry on was 8.5 kg little more than allowable. At jfk airport check in they did not let me carry it . I was little disappointed.

More leg room and comfortable seats at least for long flights

The entertainment selections are amazing. But the live TV is sometimes spotty. If you’re going to have it, then have it. If you can’t make it consistent, then, perhaps it’s better not to have it. The crew are always cordial when approached, but they seem to do the minimum and sit around, talking to each other in the back of the plane during the flight. I realize that delays are not always predictable, but I missed my flight in Dubai because we left 90 minutes late from Washington. I will say that Emirates took very good care of me in Dubai. But I would rather not be delayed.

Probably the best flight I’ve ever been on. Emirates first class is leagues beyond British airways and Lufthansa’s.

Great flight. Comfortable seats, courteous service, and excellent selection for entertainment.

Serving food took so long . Almost time close to lend. Plus during landing air pressure in cabin cuss ear blocked took long time to unblock.

Emirates is usually on time, but not this trip. Also, during the flight the attendants disappear unless called upon. Very strange. I have watched the quality of Emirates service diminish over the last five years.

Wish we had music during take off and landing like the last flight

Crew is ok. They offered food n drinks. Had difficulty connecting to wifi on board.

Great. Porter is very efficient, welcoming, and organized. I fly Porter often.

Flight was smooth and comfortable. The crew were exceptional. Amanda, Nichole and Hershel were attentive to our every need. So friendly. My daughter and I were surprised at quality of service. Loved the double row seating. Snacks were delicious. We would definitely fly with Porter again. Flight PD 670 SFO to YYZ Thank you so much for the best flight experience we have had

The E195-E2 is a great aircraft! Leather seats, lots of legroom and SO quiet! The flight crew is terrific!

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

Flight delayed 6 hr. Looking for compensation and will claim for it.allow US people to fix to avoid huge delay having a canadian tech to fix it.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10

Flight Ottawa to Toronto canceled and no crew was available to direct me on what to do. I opened a file and I wait to be compensated.

I had checked in online the day before but was instructed to collect our boarding passes when we arrived. I am not completely comfortable using the automated Kiosks and always enjoy the nostalgia of speaking with someone when checking in for a flight. Upon doing so however, we were immediately asked,"did you check in online already?" To which I replied, "yes, but we were asked to retrieve our boarding passes upon arrival." She then said, "that's what those machines over there are for. We really encourage people to use those." That unfortunately sparked a series of shortness and overall poor behavior in my opinion from the woman who checked us in. I understand it was early in the morning but I am always excited to experience flying and that interaction has unfortunately left a bitter taste in my mouth to the point I will forever now hesitate to book with Porter again. Thank you for taking the time to read this. Cheers, JD

Eine Toilette der Business Class war gesperrt und somit nicht benutzbar.

One thing is very important is you people not giving seat arrangement together to couple, senior citizen. You have to take care of senior citizen. Do not look about money. Money is not important everywhere. Make relationship strong is very very important. I like Etiyad air line out of all air line. Food was hot and delicious. Air hostess gave very good service, nice attitude, very good behaviour. I gave 10 out of 10 marks. Thanks Jivraj

Entertainment did not work from flight from Abu Dhabi to Kolkata. Emirates has a much better flight in that sector.

Ripped off and broken seats in Business class. Seats stink and need to request the staff for additional bedsheets. Crew if very friendly though

Boarding was quick and efficient. Ground staff were pleasant and courteous. Food was tasty, portions were good for me. Food containers kept slipping on the tray. Tray would look better with an anti-skid tray mat. I had the bulkhead seat which was very uncomfortable for couple of reasons. Aircraft is designed with no throughput to move across aisle to aisle. Passengers kept jumping over my legs to get from one side to the other to use the toilet. Secondly I had a mother and 9 month baby next to me. Mom had to hold baby for 12 hours in her lap as he did not fit into the bassinet. Half the baby was on my lap during the flight. Aircraft temperature was very cold - light attendant said it was the central cooling and nothing could be done about it. Movie selection was very poor old and outdated.

Crew member took too long time to take back leftover food plates from passenger seats. Food was nice.Easy excellent checking.Guy at checking counter was really kind and helpful.Made our checking very quickly. Leftover food should be taken back ASAP. Because in economy class passanger have narrow space . In the long journey like this, passanger have difficulties to sit with the plates.overall experience was good.

Everything is good and improved and needs to improve economy class seat more specious so long journey we can enjoy and it will be give more relaxable. Overall all services good and safely landed . I enjoyed my journey and all the cabin crew members services very well.

Crew did not cooperate… I just asked water twice for one crew member and she didn’t get anything.. and when I asked other crew member he gave me water and he was not respectful.. I kept Hindu non veg meal chicken .. when I get my turn chicken was not provided and then they gave me veg paneer and green peas curry which I don’t like..

Sits are very uncomfortable and food quality should be improved. Alcohol you have to ask and wait for more then 1/2 hrs. Don’t feel like to travel in Etihad. It was 1st time we traveled in Etihad now we decided we don’t want to travel in Etihad.

Very very bad service very tight seats never ever flying with Etihad again

My second flight ended up being through United and it was fine. Again, just frustrating that it was so late.

My experience was pretty frustrating because the first leg of my flight on United (though booked through Air Canada) was delayed causing me to miss my connecting flight on Air Canada. This could have been an easy solve as there was a direct flight later that morning via Air Canada that they easily could have put me on which would have only gotten me to my destination 2 1/2 hours later but because United and Air Canada don’t seem to have good communication they gave me the run around both telling me to talk with the other which I did three times to no avail. I ended up taking the delayed flight and getting on a new connecting flight which ended up getting me to my destination 6 hours later and I missed the event I was planning to go to this evening.

Everything went smoothly and as expected. We were on time and one flight arrived early.

First time flying Air Canada and the trip was very pleasant! They did a great job getting us out of Toronto and into Rome (early!) For an international flight it was very enjoyable.

This is not a Business Class equipped airplane and even the crew apologize before take over BUT BUT Air Canada charged full business class fare

All was good, except our baggage was lost for most of a day. We are thankful that it was found quickly and delivered to our hotel. Rouge was fine outside of that problem.

You do not have a space for flight cancelled. BUT!!! Air Canada handled it great. Was booked on another airline for the next day. The original flight was booked solid. But he precheck by the maintenance found a mechanical problem and the plane was not safe to fly. It was an inconvenience to have to wait until next day but I would rather arrive safely.

Very good other than we have to wait for one crew and we’re delayed and the pilot and his co- pilot has to make a difference to be right on time arrival. Disappointed about no food service also.

I had written all my complaints on my trip from Grand Junction to Denver so I will repeat it here! I was absolutely appalled that I had to pay for a regular seat that I choose 24 hrs before boarding! Also I checked my large bag which I had to pay for as well, and by the time I boarded all the room in the bins were gone so also had to check that one. I noticed people pulling out oversized suitcases, bigger than the measurements stated for carry on, and also large pack packs stuffed full! So these people were taking up 2 or 3 spaces that the rest of us should have been able to use but couldn’t! NoTV on the flight! Thankfully I had downloaded the United Airlines app and was able to watch movies on my phone. Don’t remember the last time I flew in a plane with no movie screens!

I was appalled to have to pay for just a regular seat when I went to book 24 hrs before my flight! Because it was only an hour flight I didn’t choose a seat from Grand Junction to Denver, but I did for Toronto and had to pay just to choose a regular available seat! In my 60+ years of flying this was the first time I have heard of this. Also, allowing people to bring on “huge “ suitcases, not carry on size, but much bigger, and then a large pack pack stuffed. So they take up all the room in the overhead bins and if we are later boarding, there is no room so we have to check our small carry on. I have already paid for and checked in one bag! I certainly will not choose to fly with United again unless it is the “only” airline available!

Communication was terrible. Flight was delayed for 4-5 hours in DC (on the front end, and also after we boarded, we had to get off - some issue with fueling the old plane correctly). There was little to no information on timing or what was happening. Once we reach Delhi airspace, apparently there was weather that caused us not to land - we were actually near the ground, saw the run way, and lifted back up to the sky after being sooo close. Then we circled for about 30 minutes, and they decided to go to Jaipur to land until the weather cleared and to refuel. Again, once we landed in Jaipur (wrong city), there was little to no information on timing or what was happening. Then we heard that the crew was reaching their 24 hours. We sat on the place, on the tarmac for another 3 HOURS, with no food and not enough water for everyone on the flight. Then, they kicked us off the plane with no plan, in the wrong city. We went thru customs, got our bags (thank goodness), and had to ask a bunch of staff what was happening and what to do. Eventually, their soltuion was to bus people back to Delhi (like 6 hours we were told) but not everyone would fit on the bus, and unknown timing on when it would leave. At this point it was 9PM (we were scheduled to arrive in Delhi at 11AM...). My husband and I decided to risk it and take a cab that we had to pay ourselves (about $200 US dollars) to get to Delhi (about 5 hour drive). We both had terrible trips back to the US as well - almost missed connecting flight, forced to pay for carry-on luggage (a small back pack!) and duty-free goods by the Air India staff last minute. Just terrible experience all around. Never again with AI! The ONLY good thing was the air hostesses were kind and patient - example: they made sure people with food allergies got their correct.

It would have been perfect if there was onboard entertainment.

Food was unfit even for prisoners. larger front seats are terribly uncomfortable, which is ironic. Thorough need to upgrade aircraft on such a long route.

Food could be better they need a better caterer in DC flight from India always has better food

Everything! To start with, seats, food tray table, entertainment console all are broken! Imposing duty free baggage fees for $250 as a surprise penalty cannot be appreciated! Airlines should be responsible for transferring the checked baggages to the connecting flight. Having customer go through the transfer is painful considering the travel tiredness! No soft drinks served on flight is another crumble!

Old creaky plane, poor entertainment, USB port did not work. Food was ok.

Old fittings. Went business class. Staff not very considerate regards comfort.

Very old plane. Broken tray tables n seats. Entertainment system super slow to operate and very little content.

Service was good, crew response was prompt. The baked fish and Malay fish as well as the sauces with them were bland.

Screen are not working. Windows not clean. Staff is very good. Food is okay. Experience is good. I hope the up coming is more then betters for others airlines thank you.

Book cheap domestic flights from Chicago

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9h 02mFLL-ORD
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2h 37mLGA-ORD
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2h 55mORD-MCO
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14/5Tue
directSpirit Airlines
3h 06mORD-FLL
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3h 10mFLL-ORD
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multi-stopSpirit Airlines
14h 02mMCO-ORD
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directFrontier
2h 55mORD-MCO
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directFrontier
3h 07mMCO-ORD
C$ 385
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multi-stopUnited Airlines
22h 28mORD-EWR
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directUnited Airlines
2h 40mEWR-ORD
C$ 495
14/5Tue
multi-stopUnited Airlines
8h 38mORD-EWR
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directUnited Airlines
2h 40mEWR-ORD
C$ 500
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directAmerican Airlines
2h 09mORD-LGA
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multi-stopAmerican Airlines
6h 51mLGA-ORD
C$ 628
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directAlaska Airlines
4h 34mORD-SEA
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directAlaska Airlines
4h 00mSEA-ORD
C$ 796
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multi-stopAmerican Airlines
9h 47mORD-LAS
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multi-stopAmerican Airlines
6h 22mLAS-ORD
C$ 819
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directAlaska Airlines
4h 34mORD-SEA
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3h 59mSEA-ORD
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Recent round-trip flight deals

26/5Sun
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4h 02mORD-LAS
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3h 41mLAS-ORD
C$ 157
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4h 00mORD-LAS
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directSpirit Airlines
3h 47mLAS-ORD
C$ 172
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32h 04mLAS-ORD
C$ 251
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9h 39mLAS-ORD
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multi-stopAlaska Airlines
7h 17mORD-LAS
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7h 41mLAS-ORD
C$ 302
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17h 57mORD-LAS
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multi-stopAlaska Airlines
7h 41mLAS-ORD
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8h 08mLAX-ORD
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multi-stopAlaska Airlines
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multi-stopSpirit Airlines
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directUnited Airlines
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Flights from Chicago to Anywhere

Cabin classes:

C$ 1,271
C$ 1,171
C$ 1,359
C$ 36

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