Find deals on flights from Chicago from $40
This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight departing on 8/2. 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.Round-trip
1 adult
Economy
Sat 6/24
Sat 7/1
Here is why travelers choose KAYAK
Save 22% or moreCompare multiple travel sites with one search.
Free to useThere are no hidden charges or fees.
Filter your dealsChoose cabin class, free Wi-Fi and more.
Search hundreds of travel sites at once for cheap international flights from Chicago
...and more
Where can I fly from Chicago?
Prices from CHI, departing Sat 6/24 and returning Sat 7/1Good to know
Low season | January |
|---|---|
High season | June |
Cheapest flight | $40 |
Average price round-trip | $429 |
Good deal round-trip | $96 |
Good deal one-way | $58 |
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from Chicago O'Hare Airport to Miami
(avg. price over the last 2 weeks)
or less
or less
Top tips for finding a cheap flight out of Chicago
- Book at least 2 weeks before departure in order to get a below-average price.
- High season is considered to be June and July. The cheapest month to fly from Chicago is January.
- Morning departure is around 6% cheaper 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.
FAQs for booking flights out of Chicago
Top 5 airlines serving from Chicago to Anywhere
Scores according to KAYAK customer reviews8.3
Alaska AirlinesOverall score based on 29426 reviews
83comfort
88crew
85overall
85boarding
79entertainment
79food
Airline reviews
Pros: "Timing of the flight was always good. Efficient flying. Crew was super helpful too even when passengers were a bit too much."
Pros: "Timing of the flight was always good. Efficient flying. Crew was super helpful too even when passengers were a bit too much."
Pros: "The attendant at the gate was great about getting me a seat assignment next to the other person in my group. The food options on the flight are much better than I expected for airplane food."
Cons: "No complaints, really."
Pros: "The crew did very well. The seats could have been a little more comfortable, the lumbar could have been a bit more stiff for lower back support, the arm rest up and down function did not work, and a little more space between rows and seats would have made it more comfortable."
Cons: "The seats could have been a little more comfortable, the lumbar could have been a bit more stiff for lower back support, the arm rest up and down function did not work, and a little more space between rows and seats would have made it more comfortable. The bathroom was too narrow."
Pros: "The Crew from check in to flight was amazing! Service with a Big huge smile."
Cons: "Nothing to dislike."
Cons: "Delayed. Flue season folks. If your sick just don’t travel!"
Pros: "Leg room seems a bit more spacious than other flights. Very comfortable. Nice experience."
Pros: "Nothing."
Cons: "We were sitting in the plane on the tarmac for 3 hours waiting to take off. The crew did a very poor job announcing what was going on."
Pros: "Alaska airlines much better than United or American in terms of friendly service, wifi and battery charge, and entertainment options"
Pros: "Crew was friendly, attentive, and informed us of any delays going on. Great experience!"
Cons: "The flight attendant went on and on and ON about how turbulent air was reported ahead, just because we're in a smooth stretch doesn't mean we're out of it yet, and so on. Must have been every 10-20 minutes. She just would not stop talking; while her voice was fine in person, over the PA it sounded like a cheese grater taken to my inner ear. I barely slept that flight; it was miserable."
Cons: "The seats were awful and uncomfortable. Payed 100 dollars extra for even more leg room and barely had any. Such an old plane for such a long flight. The seats in the first row barely fit a female with hips. The in-flight entertainment was staticky and you could barely see the TVs. Overall, one of the worst flights I have taken on JetBlue."
Pros: "Complimentary snacks and drinks."
Cons: "Broken seat back, broken tray table, audio input didn't work."
Pros: "Cleo, our fly attendees made us feel right at home!"
Pros: "Seats are comfortable, main reason I like this airline. Crew was nice."
Cons: "The screens on the back of the seats are showing their age and the controls on the armrests are causing your neighbor to change your channel or the brightness of the screen. Letting everyone stream content to their own devices would probably be a better option, with safe charging available."
Pros: "Crew was friendly. Food was good, especially the beef at dinner"
Cons: "Breakfast omelette was rubbery and really not good. Layover was way too long (4h). Not looking forward to my 11h layover on the way back, but at least JFK is a nice airport and I have lounge access through one of my credit cards"
Pros: "Everything was smooth, great service, friendly staff and captain. Arrived ahead of time. Free Wifi. Great inflight entertainment."
Pros: "You can always count on JetBlue for good snacks and free WiFi."
Cons: "But the snacks and free WiFi is not enough to payback the delayed departure experience. Just a week prior, my JetBlue flight was scheduled on time and then three things delayed thre flight for three hours right before we took off and now this! I was told it was due to needing to replace a crew member from another delayed flight. How can that affect so many people? The seat was also super uncomfortable and the back of the cushion was rolling forward, which made it hard to sit for that long. we also didn’t have a gate when we landed so that added on an extra 30minutes. Really disappointed."
Pros: "The flight was very smooth and the staff was very nice."
Cons: "The wifi did not work at all and my TV did not work so I had to listen to my music the entire trip."
Cons: "My first flight was delayed an hour due to pilot error (we left the gate on time, but sat on the tarmac for an hour). This caused me to miss my connecting flight, which stranded me at JFK because they only had one flight per day to my destination. JetBlue's customer service told me I could not reach my destination until the next day, which was unacceptable (I had a morning interview). In fact, the only thing they said they could do was *PARTIALLY* refund my ticket, even though they stranded me in a completely different city. They also said I would "be able to" book a new flight with a different carrier, which cost roughly $400, using my own money. In the end, I spent about an hour talking with customer service until they were "nice enough" to do a partial refund with an additional credit equaling the remainder of my $400 ticket to fly with them in the future. It was still a very poor interaction with customer service."
Pros: "I appreciate that they let families with strollers board after Group A, there seems to be more space than the major carriers, and the snacks are good!"
Cons: "My Satellite XM radio didn’t seem to be working."
Pros: "Kosher snacks! Thank you. Screens and outlets at every seat. Safe, controlled Covid protocols including de-boarding. Excellent!"
Pros: "The crew’s positive energy and great service were truly amazing. Kudos Delta!"
Cons: "We arrived around 39 minutes early and the whole process was very smooth"
Pros: "When I asked for a seat change the crew was very accommodating"
Cons: "With covid in Seattle I was placed next to a restroom. I did not see any bathroom sanitation occurring during the flight, and no sanitizer available anywhere."
Pros: "Super friendly and helpful with connections."
Cons: "The music on the plane was a bit much. Lol"
Cons: "Turn on the lights before landing graduallyb- noone likes bright fast - too nasty;"
Pros: "Nothing"
Cons: "We were traveling international in Twitter after contacting we were told we can carry one checked baggage but then we were not allowed and at gate they didn’t know the procedure and repeatedly checked our passport Poor customer service"
Pros: "Flight was good and crew were good. Nothing very outstanding but by no means a terrible flight."
Cons: "The in flight screens weren't working well."
Pros: "No"
Cons: "The flight was delayed almost 6 hours, the crew was rude and the “comfort +” seats had very little leg room ."
Pros: "Very nice, pleasant crew."
Cons: "Extended turbulence was very uncomfortable. One toilet out of service. Otherwise good flight."
Pros: "It didn’t smell bad"
Cons: "It was way too cold and my seat was broken so it didn’t recline"
Pros: "Boarding was a breeze. The staff was friendly and fast. The seats were comfortable (although, I am 5’2”)."
Cons: "I can’t complain this time around!"
Pros: "Nothing"
Cons: "I was not informed about the delay, no on board entertainment, missed work due to delay and landed 2 hours late!"
Cons: "The flight was delayed for several hours due to a severe thunderstorm from MSP to JFK. The airline crew failed to update all passengers so most of us were just aimlessly pacing around the gate. The team was very disengaging, not sincere, and not professional. This was definitely a -1 customer experience as many customers complained, missed connecting flights, or like myself - had to call my office at an ungodly hour and explain that i’d be missing work"
Cons: "There were not enough agents at the airport to check us in. The lines were long and passengers became surly."
Cons: "Many things. Did not tell me that even carry on was a 25.00 charge. After check in, counter woman at Sun County sent me to a security station on a far side of airport that was closed. Plane delayed. Plane bathroom issues"
Pros: "Nice Staff"
Cons: "They charge for everything the planes are a bit outdated, boarding is backwards they load middle bank then front very weird."
Pros: "The crew was friendly and boarding was quick, seats were comfortable and plane was clean"
Cons: "No snacks included, bags of pop chips was $3. No entertainment on the plane (I ended up just sleeping anyway). They didn't have space for everyone's carry on and asked for volunteers to check their bags but didn't enforce any rules for people who had 3+ carry on items"
Pros: "4 1/2 hour late boarding! Missed my connecting flight and was stuck!"
Cons: "Had a 4 1/2 hour delay from Minneapolis to NY city. Which of course cause me to miss my flight to Europe. There was no attempt to find another flight that would get me there in time. By the time I got to NY it was close to Midnight, and the only hotel available was 40 mins away from the airport at an additional cost of $270 for the room and uber rides. No compensation even offered or provided for extra expenses they caused by us leaving so late. Thank you Sun Country for starting my vacation off so well."
Pros: "More friendly cabin crew a must for sustaining the airlines business.!!!"
Cons: "The toilets needs to be cleaned at more freqfrequency."
it was a nightmare of a trip. multiple delays, dirty bathrooms, long wait in tarmac, ran out of fuel diverting flight. on and all over 4 hour delay!
Horrible scam. Make you pay extra for more leg room then switch your seat as you’re boarding to a regular seat. Never fly American!
Pros: "The plane was really clean and they had lots of overhead storage."
Cons: "It was too crowded and cramped and UNCOMFORTABLE and there was a REALLY LOUD kid that would not shut up and nothing was done about it."
Pros: "The plane is amazing and the crew was very nice and helpful"
Cons: "Everything was all good."
Pros: "Despite the poor rating because of the mechanical issue, I will say the pilots did a fantastic job with some pretty choppy air conditions."
Cons: "Flight was delayed almost an hour while we were already on the plane. Minor mechanical issue that could’ve been handled at destination. The seat was super uncomfortable and I would’ve appreciated at least some more from the crew, like maybe even a bottle of water or something."
Pros: "Crew was excellent especially the first class attendant very attentive and always checking on you"
Cons: "The food needs to be back to normal for first class and also baggage is very slow almost over 30 min wait"
Pros: "Punctuality, professionalism, and overall excellent customer service. Every personal i spoke with was very helpful and pleasant."
Cons: "There are too many good flight times with extensive layovers not enough non stop flights at reasonable times"
Pros: "The crew was fine, friendly enough, although I was incredibly disappointed that they didn't force people to wear their masks as they boarded. They also didn't enforce masks over noses--rendering masks useless."
Cons: "The flight was completely full. And people weren't wearing masks as they boarded, and the flight attendants did nothing about that. Also, there was no distancing IN the airport during boarding. It's NOT DIFFICULT to put tape marks on the ground to ensure physical distancing. It is THEIR responsibility to make sure the process is safe, since half of the people seem to not care about distancing (or mask wearing). I'm incredibly disappointed and I will be flying Southwest for the time being: I hear they're better at enforcing distancing."
Pros: "The crew was nice"
Cons: "There was maintenance happening on the plane after everyone boarded. It was a long wait on the plane and it could have been better if that was done before boarding."
Cons: "Baggage delivery was slow and then split between 2 different terminals"
Book cheap domestic flights from Chicago
Recent round-trip flight deals
7/4Tue
nonstopSpirit Airlines
3h 09mORD-MIA
7/11Tue
nonstopSpirit Airlines
3h 23mMIA-ORD
$88
9/23Sat
nonstopSpirit Airlines
4h 04mORD-LAS
9/26Tue
nonstopSpirit Airlines
3h 35mLAS-ORD
$88
6/13Tue
nonstopSpirit Airlines
3h 09mORD-MIA
6/21Wed
nonstopSpirit Airlines
3h 23mMIA-ORD
$90
6/7Wed
nonstopSpirit Airlines
3h 00mORD-MIA
6/7Wed
nonstopSpirit Airlines
3h 23mMIA-ORD
$92
7/4Tue
nonstopSpirit Airlines
3h 00mORD-MIA
7/11Tue
nonstopSpirit Airlines
3h 23mMIA-ORD
$93
6/6Tue
nonstopSpirit Airlines
3h 11mORD-MIA
6/7Wed
nonstopSpirit Airlines
3h 23mMIA-ORD
$95
8/24Thu
nonstopUndisclosed Carrier
2h 23mORD-DFW
8/29Tue
nonstopUndisclosed Carrier
2h 36mDFW-ORD
$98
9/12Tue
nonstopDelta
2h 05mORD-LGA
9/13Wed
nonstopDelta
2h 49mLGA-ORD
$105
9/7Thu
nonstopUnited Airlines
2h 14mORD-EWR
9/19Tue
nonstopUnited Airlines
2h 39mEWR-ORD
$106
8/15Tue
nonstopJetBlue
2h 16mORD-JFK
8/23Wed
nonstopJetBlue
2h 38mJFK-ORD
$106
8/23Wed
nonstopDelta
2h 13mORD-LGA
8/30Wed
nonstopDelta
2h 41mLGA-ORD
$106
8/23Wed
1 stopUndisclosed Carrier
5h 22mORD-FLL
8/29Tue
nonstopUndisclosed Carrier
3h 15mFLL-ORD
$106
8/18Fri
1 stopUndisclosed Carrier
14h 15mORD-DFW
8/21Mon
nonstopUndisclosed Carrier
2h 36mDFW-ORD
$108
6/27Tue
nonstopUndisclosed Carrier
2h 28mORD-DFW
7/26Wed
nonstopUndisclosed Carrier
2h 32mDFW-ORD
$109
8/24Thu
nonstopUnited Airlines
2h 09mORD-LGA
8/28Mon
nonstopUnited Airlines
2h 38mLGA-ORD
$120
6/5Mon
1 stopMultiple Airlines
21h 28mORD-MIA
6/7Wed
nonstopMultiple Airlines
3h 23mMIA-ORD
$125
6/7Wed
1 stopMultiple Airlines
9h 27mORD-FLL
6/14Wed
1 stopMultiple Airlines
14h 04mFLL-ORD
$131
8/23Wed
nonstopJetBlue
2h 16mORD-JFK
8/29Tue
1 stopJetBlue
6h 14mJFK-ORD
$136
6/5Mon
1 stopFrontier
12h 10mORD-LAS
6/7Wed
1 stopFrontier
11h 03mLAS-ORD
$151
7/3Mon
nonstopAmerican Airlines
2h 04mORD-LGA
7/6Thu
nonstopAmerican Airlines
2h 33mLGA-ORD
$168
Search by stops
Search by airline
Search by price
Recent one-way flight deals
8/2Wed
nonstopSpirit Airlines
3h 00mORD-MIA
$40
6/7Wed
nonstopSpirit Airlines
3h 09mORD-MIA
$41
7/25Tue
nonstopSpirit Airlines
3h 09mORD-MIA
$42
7/11Tue
nonstopSpirit Airlines
3h 09mORD-MIA
$43
6/5Mon
1 stopUndisclosed Carrier
5h 57mORD-FLL
$44
7/25Tue
nonstopSpirit Airlines
3h 09mORD-MIA
$44
6/24Sat
nonstopSpirit Airlines
3h 55mORD-LAS
$44
6/12Mon
nonstopUndisclosed Carrier
3h 08mORD-FLL
$51
8/15Tue
nonstopDelta
2h 05mORD-LGA
$53
9/8Fri
nonstopUnited Airlines
2h 19mORD-EWR
$53
8/15Tue
nonstopJetBlue
2h 16mORD-JFK
$53
6/7Wed
nonstopUndisclosed Carrier
2h 28mORD-DFW
$53
7/12Wed
nonstopUndisclosed Carrier
2h 28mORD-DFW
$54
6/13Tue
1 stopMultiple Airlines
20h 49mORD-MIA
$66
8/24Thu
nonstopUnited Airlines
2h 09mORD-LGA
$67
6/6Tue
1 stopFrontier
8h 54mORD-LAS
$70
8/9Wed
nonstopAmerican Airlines
2h 08mORD-EWR
$84
6/6Tue
1 stopSouthwest
6h 45mORD-HOU
$123
9/4Mon
nonstopAlaska Airlines
4h 32mORD-SEA
$124
10/26Thu
1 stopSun Country Air
12h 26mORD-JFK
$138
Search by stops
Search by airline
Search by price
Book cheap international flights from Chicago
Recent round-trip flight deals
10/17Tue
nonstopFrontier
4h 03mORD-CUN
10/26Thu
nonstopFrontier
4h 00mCUN-ORD
$161
9/5Tue
nonstopFrontier
3h 50mORD-CUN
9/12Tue
nonstopFrontier
4h 04mCUN-ORD
$188
6/4Sun
nonstopFrontier
3h 49mORD-CUN
6/7Wed
nonstopFrontier
4h 00mCUN-ORD
$189
6/4Sun
nonstopFrontier
3h 49mORD-CUN
6/8Thu
nonstopFrontier
4h 00mCUN-ORD
$190
8/27Sun
nonstopFrontier
3h 50mORD-CUN
8/31Thu
nonstopFrontier
4h 02mCUN-ORD
$194
6/19Mon
nonstopSpirit Airlines
3h 31mORD-CUN
6/24Sat
nonstopSpirit Airlines
4h 11mCUN-ORD
$195
6/4Sun
nonstopUndisclosed Carrier
3h 49mORD-CUN
6/7Wed
nonstopUndisclosed Carrier
4h 00mCUN-ORD
$196
6/5Mon
nonstopMultiple Airlines
3h 33mORD-CUN
6/9Fri
nonstopMultiple Airlines
4h 00mCUN-ORD
$205
9/2Sat
1 stopMultiple Airlines
17h 38mORD-CUN
9/21Thu
nonstopMultiple Airlines
4h 04mCUN-ORD
$209
6/5Mon
nonstopSpirit Airlines
3h 33mORD-CUN
6/13Tue
nonstopSpirit Airlines
4h 11mCUN-ORD
$211
6/6Tue
1 stopUndisclosed Carrier
14h 27mORD-CUN
6/8Thu
1 stopUndisclosed Carrier
8h 57mCUN-ORD
$212
6/5Mon
nonstopMultiple Airlines
3h 33mORD-CUN
6/9Fri
nonstopMultiple Airlines
4h 00mCUN-ORD
$214
7/9Sun
nonstopMultiple Airlines
3h 49mORD-CUN
7/12Wed
nonstopMultiple Airlines
4h 11mCUN-ORD
$215
6/27Tue
nonstopSpirit Airlines
3h 31mORD-CUN
6/29Thu
nonstopSpirit Airlines
4h 11mCUN-ORD
$216
7/9Sun
nonstopUndisclosed Carrier
3h 49mORD-CUN
7/12Wed
nonstopUndisclosed Carrier
4h 11mCUN-ORD
$217
6/6Tue
nonstopUndisclosed Carrier
3h 49mORD-CUN
6/8Thu
nonstopUndisclosed Carrier
4h 00mCUN-ORD
$218
9/2Sat
1 stopVolaris
18h 51mMDW-CUN
9/20Wed
1 stopVolaris
13h 36mCUN-MDW
$234
9/4Mon
1 stopVolaris
18h 51mMDW-CUN
9/19Tue
1 stopVolaris
10h 38mCUN-MDW
$238
6/26Mon
1 stopDelta
13h 49mMDW-CUN
6/29Thu
1 stopDelta
9h 01mCUN-MDW
$265
6/27Tue
1 stopAeromexico
9h 40mMDW-CUN
7/5Wed
1 stopAeromexico
9h 42mCUN-MDW
$276
Search by stops
Search by airline
Search by price
Recent one-way flight deals
8/22Tue
nonstopFrontier
3h 50mORD-CUN
$75
6/3Sat
nonstopFrontier
3h 49mORD-CUN
$76
8/14Mon
nonstopFrontier
3h 50mORD-CUN
$82
9/5Tue
1 stopVolaris
17h 06mORD-CUN
$85
8/14Mon
nonstopUndisclosed Carrier
3h 50mORD-CUN
$87
6/28Wed
nonstopSpirit Airlines
3h 31mORD-CUN
$95
6/3Sat
nonstopFrontier
3h 49mORD-CUN
$96
6/6Tue
nonstopSpirit Airlines
3h 33mORD-CUN
$98
6/21Wed
nonstopSpirit Airlines
3h 31mORD-CUN
$99
7/9Sun
nonstopFrontier
3h 49mORD-CUN
$101
8/24Thu
nonstopUndisclosed Carrier
3h 50mORD-CUN
$106
6/1Thu
nonstopUndisclosed Carrier
3h 33mORD-CUN
$108
6/2Fri
nonstopUndisclosed Carrier
3h 33mORD-CUN
$112
7/8Sat
1 stopUnited Airlines
15h 57mORD-CUN
$119
8/23Wed
1 stopAeromexico
16h 05mORD-CUN
$121
6/28Wed
1 stopDelta
6h 35mMDW-CUN
$124
6/28Wed
1 stopDelta
12h 29mORD-CUN
$124
8/14Mon
1 stopDelta
5h 20mMDW-CUN
$125
6/3Sat
2 stopsAeromexico
24h 27mORD-CUN
$130
6/23Fri
2 stopsMultiple Airlines
36h 11mMDW-CUN
$151