Planning a trip from Chicago to Miami? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.
When planning a flight from Chicago to Miami, it's important to note that Tuesdays and the month of September are generally the cheapest times to fly.
Cheapest Route: Opt for flights from Chicago Midway to Miami for the most affordable option.
Booking Time: To save money, book your flight at least 20 days in advance.
Budget Airline: Consider flying with Spirit Airlines, as they generally offer the cheapest fares.
Flight Type: Direct flights are significantly cheaper than those with one stop.
AI-powered; AI can make mistakes.
| Low season | September |
|---|---|
| High season | March |
| Cheapest flight | $41 |
Direct departures
Chicago to Miami
Monday
American Airlines, Frontier, Southwest, +2 more
American Airlines, Frontier, +3 more
1
2
Tuesday
American Airlines, Southwest, Spirit Airlines, +1 more
American Airlines, Southwest, +2 more
1
Wednesday
American Airlines, Frontier, Southwest, +2 more
American Airlines, Frontier, +3 more
1
2
Thursday
American Airlines, Frontier, Southwest, +2 more
American Airlines, Frontier, +3 more
1
2
Friday
American Airlines, Frontier, Southwest, +2 more
American Airlines, Frontier, +3 more
1
2
Saturday
American Airlines, Frontier, Southwest, +2 more
American Airlines, Frontier, +3 more
1
2
Sunday
American Airlines, Frontier, Southwest, +2 more
American Airlines, Frontier, +3 more
1
2
Direct returns
Miami to Chicago
Monday
American Airlines, Frontier, Southwest, +2 more
American Airlines, Frontier, +3 more
1
2
Tuesday
American Airlines, Southwest, Spirit Airlines, +1 more
American Airlines, Southwest, +2 more
1
Wednesday
American Airlines, Frontier, Southwest, +2 more
American Airlines, Frontier, +3 more
1
2
Thursday
American Airlines, Frontier, Southwest, +2 more
American Airlines, Frontier, +3 more
1
2
Friday
American Airlines, Frontier, Southwest, +2 more
American Airlines, Frontier, +3 more
1
2
Saturday
American Airlines, Frontier, Southwest, +2 more
American Airlines, Frontier, +3 more
1
2
Sunday
American Airlines, Frontier, Southwest, +2 more
American Airlines, Frontier, +3 more
1
2
The staff was very friendly, professional, and courteous. The overall flight was a great experience.
The staff was very friendly, professional, and courteous. The overall flight was a great experience.
Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.
They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.
Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.
All was good. I just had a hard time getting connected to the WiFi/internet during the flight
Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.
The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.
after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though
I'm not a fan of Southwest's model. I don't like the herding style of boarding.
It is southwest seat was ok. Not the most comfortable seat
Short flight, but no drink/snack service. The flights both going and coming were delayed.
Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd
I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.
In overall it was a good experience, the only down point was that the entertainment screen was working properly.
They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!
I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...
cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.
Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/
Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.
I liked the snacks and the flight attendants were friendly.
The flight was really crowded. Flight attendants were just ok.
Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa
We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.
Attendants were pleasant and the flight was smooth and relaxed.
Delays to take off and to leave the plane after landing added a lot of time to this flight.
It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.
While waiting to claim my checked luggage, I discovered the airline had lost it. After a long wait and inquiries, I discovered it was on another flight. Fortunately, the airline finally sent my luggage home.
This flight never occurred because AA couldn’t get their act together.
During service there was a garbage/beverage spill near our seats that never was cleaned up. On a relatively short flight when we’re fortunate enough to actually have in flight movies available, the flight attendants pitching the AADVANTAGE credit card shouldn’t talk for the last 10 minutes of the flight so that we miss the end of the movie.
The boarding was pretty easy. However, the first class seats are not lay flat as other airlines (like JetBlue) has and therefore sleeping was a challenge.
Everything was terrible. Flight was delayed several hours, crew was abrasive. Stuck on runway for over a hour. There was an argument between passengers that nearly turned into a fight while waiting to exit plane, crew did nothing. Took nearly 3 hours to retrieve luggage at baggage claim. Lost an entire day of vacation. Will never fly spirit again under any circumstance
All of our flights were canceled, though every other airline was flying out and in
Paid for wifi the day before but wifi was unavailable on flight.
it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .
Bad experience with gate agent. I asked what group she was boarding. She gave me a face and said, with attitude, group 1. I stood back and waited for my group, group 2 to be called. After an awful lot of people boarded she took the mic and announced, now boarding group 5. The lack of professionalism amongst spirit staff is astounding.
Spirit Airlines has a reputation for being a terrible, cheap airline, this is why. I took a gamble on them, having never flown with them before, and the flight got cancelled. First they delayed the flight about 4 times before finally canceling it because a flight attendant didn’t show up to work that day. That’s so stupid. When I asked a ticketing agent she said that’s “company policy”. A company policy that inconveniences hundreds of passengers because a single flight attendant didn’t show is ridiculous and inefficient. I will never, ever try flying Spirit Airlines again.
Flight was cancelled with no help From spirit or kayak. Please refund asap
I love a flight without turbulence and you guys deliver It’d be nice to have comfier seats and maybe some inflight entertainment and snacks but that’s for Delta
Cancelled my flight and the earliest that they are willing give me for the next flight which was 3 days later on a weekday. Only accommodation they are willing to give was $30 airline credit that will expire in 1 year
Flight was canceled, huge lines to get baggage returned. Most other airlines had delays but not widespread cancellations like Spirit.
I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.
One of the worst travel experiences I've had. Had a flight scheduled with CVG to RSW on VLSWQX this morning departing at 5:30. Two individuals at the gate and one was in training. Not her fault but she didn't have the ability to check people in resulting in at least 15 families that didn't make it on the plane because they weren't checked into the system in time. When arriving at the airport to drop off our prepaid checked bags, the bag drop off agent asked if we could check our bags at the gate because of the long line. We said no problem so arrived at the gate by 5:00. They told those people that had previously paid for checked bags to stand off to the side while they let others that either didn't have a checked bag or their bag was already on the plan through. Realizing the gate workers had an issue, they either called for help or this lady showed up late for work as she didn't arrive until 5:15. The worker who had been there training the other individual and working diligently to make sure all passengers got on board. He even said that at one point all people that are currently in line are fine but asked the person in training to stand outside the ticketing area around 5:15 to notify any late travels that the flight was in boarding process and they arrrived too late. At that point, we're sill standing off to the side with our pre-paid checked bags patiently waiting. When the new lady arrived she couldn't have been more rude. It was an awful seen. Essentially they had asked for those without an assigned seat to board last, those with pre-paid checked bag stand off to the site and any traveling with a larger items that needed to be checked at the gate (such as a stroller), wait on the side. They realized that the flight needed to leave on time so the gate attendant shut the gate. So anyone without a seat assignment, those that had pre-checked bags, and the worst one I saw was a mother with two infant children was in line with use because she was asked to stand to the side because her stroller. When they shut the door to the plan they told her she could no longer get on. Her checked bags were already on the plane with her car keys in them, and the lady told her we couldn't accept anyone else on because the door was shut. She didn't even have a way to get home from the airport. Truely evil behavior. I've flown Frontier enough to know customer service is not a top priority in the company's mission, but this was an all-time low. I'm sending this after an 18 hour drive that our family just completed to Bonita Springs . I felt really bad for the lady being trained and the other individual trying to help, but when the new lady came to the gate she was truly one of the rudest individuals I've ever met. One lady had been there since 4am but because she didn't have an assigned seat they wouldn't let her on the plan.
Better than expected. Staff were friendly and nice on both flights.
Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.
No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.
It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.
Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.
Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.
Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.
I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline
| Transportation mode | Average price | Average duration |
|---|---|---|
| Flights | $552 | 3h 00m |
| Trains | $386 | 46h 29m |