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.
This feature is powered by ChatGPT: an OpenAI-developed artificial intelligence model trained with KAYAK proprietary data and third-party data not verified by KAYAK.
Low season | September |
|---|---|
High season | March |
Cheapest flight | $38 |
Find which airlines fly direct from Chicago to Miami Airport, which days they fly and book direct flights.
Nonstop departures
Monday
Aer Lingus, Air Canada, Air New Zealand, +15 more
Aer Lingus, Air Canada, +16 more
14
15
Tuesday
Aer Lingus, Air Canada, Air New Zealand, +13 more
Aer Lingus, Air Canada, +14 more
12
13
Wednesday
Aer Lingus, Air Canada, Air New Zealand, +16 more
Aer Lingus, Air Canada, +17 more
15
16
Thursday
Aer Lingus, Air Canada, Air New Zealand, +15 more
Aer Lingus, Air Canada, +16 more
14
15
Friday
Aer Lingus, Air Canada, Air New Zealand, +16 more
Aer Lingus, Air Canada, +17 more
15
16
Saturday
ANA, Aer Lingus, Air Canada, +15 more
ANA, Aer Lingus, +16 more
14
15
Sunday
ANA, Aer Lingus, Air Canada, +16 more
ANA, Aer Lingus, +17 more
15
16
Nonstop returns
Monday
Aer Lingus, Air Canada, Air New Zealand, +17 more
Aer Lingus, Air Canada, +18 more
16
17
Tuesday
Aer Lingus, Air Canada, Air New Zealand, +16 more
Aer Lingus, Air Canada, +17 more
15
16
Wednesday
Aer Lingus, Air Canada, Air New Zealand, +16 more
Aer Lingus, Air Canada, +17 more
15
16
Thursday
Aer Lingus, Air Canada, Air New Zealand, +17 more
Aer Lingus, Air Canada, +18 more
16
17
Friday
Aer Lingus, Air Canada, Air New Zealand, +18 more
Aer Lingus, Air Canada, +19 more
17
18
Saturday
Aer Lingus, Air Canada, Air New Zealand, +18 more
Aer Lingus, Air Canada, +19 more
17
18
Sunday
Aer Lingus, Air Canada, Air New Zealand, +17 more
Aer Lingus, Air Canada, +18 more
16
17
Pretty standard flight. We left late, but arrived early. The wifi entertainment is always nice. The free snacks and beverages are simple, but appreciated. I'm tall and the seats are an issue. I can deal with a short flight, but any longer, I have to find another airline where I know beforehand I have extra legroom.
Pretty standard flight. We left late, but arrived early. The wifi entertainment is always nice. The free snacks and beverages are simple, but appreciated. I'm tall and the seats are an issue. I can deal with a short flight, but any longer, I have to find another airline where I know beforehand I have extra legroom.
The flight attendant was proactive in helping with placing carry on in overhead bins. This was the first time I had ever been offered help without asking or obviously struggling. Many on the flight were older people like myself and vertically challenged. I would hope this would be the norm on all flights.
wifi wasn't working correctly so couldn't watch live tv
Flight was delayed by 12 minutes. Boarding wasn’t fun. The crew was nice though.
The flight was promptly on schedule and Southwest delivered everything they promised. No excuses for any shortfalls just 100% ownership of their responsibilities and business. The boarding and seating policy is a complete shambles. What started out as a great idea when Southwest first hit the market has been turned into a disaster due to the lack of integrity in many of the people who fly Southwest and take advantage of Southwest generosity at the expense of their fellow passengers.
Flight was delayed more than 2 hour do the scheduling issues and then some confusing weight and balance matters, followed by a miscommunication with the tower on which runway was going to be used based on the airplane weight. All these things should have been figured out in advance. Instead of arriving at 12:30 a.m. we arrived at 2:30 a.m. very difficult to find a taxi or other transport at SFO. Luggage was delayed. An extension of an unpleasant flight day
It good. Just not that plane didn’t have power outlets to charge devices etc.
Although the flight was delayed, but the crew was amazing. They did the best they could to make the time enjoyable.
My experience with Southwest as a whole was good but coming out of Cancun to Chicago it was terrible. Not only was it a language barrier with customer service we stood there to ask questions and they act like they didn't even see you. So the first come approach is not all that great anymore.
I liked the boarding by group and numbers. I didn't like my inability to guarantee our seats together. I didn't like the $8/flight for Internet, but I did appreciate the inflight movie options on their app. I didn't like that there were no charging stations on the seats during either of our flights. One flight was over 3 hours.
They need to improve their boarding process. Group 1 and/or paying first class passengers shouldn't be in the middle of boarding process
late departure due to some unspecified issue with ventilating the cabin. They got it running but it was FREEZING for the whole flight. I asked for a blanket but they didn't provide one. They could not turn up the heat. it was quite miserable.
I still prefer Delta, but Delta doesn’t fly to State College PA.
Everything was fantastic. Modern plane. All the amenities! Although the paid snacks and meals are pure robbery. Like i understand airlines need to make money, but 11$ USD for an overnight oats with some nuts in it and barely any pieces of apple.... Highway robbery
The flight was bumpy. No Breakfast or coffee was served, not even a bottle of water. The food was okay but odd. Rice with peas instead of couscous with some unknown green thing. United Airlines did not tell me that there was VERY LIMITED HANDICAP SERVICE IN NAPLES. De-plane via 20 aluminum steps. Taken to Van. You must walk into the terminal, find luggage, and then walk out to the rental car pickup spot that is 1 block from the terminal.
Crew did their best but the plane configuration is too tight if you're bigger than an average sardine. Controls for the entertainment system didn't all work. The aircraft hadn't been cleaned in awhile.
Didn't make it dir to delays - no support from United staff
No water on the toilets, dirty sits. 4 hours delayed departure.
My flight was delayed for a whole day, so I lost a day of my vacation.
flight delayed, was put on another flight after standby queue, luggage was misplaced and arrived to me 3 days later
I love to flight american however my carry on had to be sent with regular luggage and it was broken. Don't appreciate that. If when I buy a ticket says I can take a carry on and a hand item there should be space for mwsy stuff and not be basically forced to send the item even if it's at no charge. A.A. needs to work on that. Everything else excellent.
The flight was delayed which was disappointing. There was no pre takeoff refreshment in first, as we had to wait around an hour in our seats before take off that was disappointing too. The inflight entertainment/wifi did not work, and the crew were slow to offer drinks in flight
Pilots showed up late because they decided to stop and get something to eat instead of going straight to our gate, Forcing an 1 1/2 hour delay, and missed flight. Shame on the pilots.
There was a serious delay of almost 2 hrs to departure.. it would have been to be told what caused the delay. Apart from the delay, boarding and the flight itself went smoothly.
Flight departed on time and arrived a bit early. Can’t go wrong with that! And makes a travel experience go so well
The flight was quick which gave me more time to get to my other flight.
Terrible. We had about a 3 hours delay which led to us missing our connecting.
It was the worst experience ever. Cabin temperature cold, for which they did not have any blankets upon my asking. We paid $125 extra for each passenger to get extra space sits; the sits were ridiculously small, tight, and uncomfortable! The flight attendant dropped ice on me and my sister! All in all, American Airlines deserves below zero!
The inability to be flexible when you need to change a Basic Economy flight, when your company demands you book through a third party, causes raw feelings about the whole experience. A major airline should realize business and personal plans change all the time. I must save my company money on travel. Even if you have to charge me for the change, I get it. But being so rigid with a policy is not the best customer service.
Absolutely the worst experience. We were 5 hours delayed due to mechanical issues and a crew timing out. We were not offered any concession. When I asked for a meal voucher, they gave me $12. You can get a bottle of water for that at the airport. Offensive.
Everything was excellent and as expected. The boarding process was great but deboarding was a bit slow. No fault of the crew; it just seemed like the passengers didn’t want to leave! 😂
Easy! As long as you don’t mind no frills, our flight was enjoyable and on time
The flight was delayed and the announcements were hard to hear, but the crew was great
Fantastic. Had handicapped traveler and they helped us through security, helped with boarding, helped put wheelchair together, and were all very patient. A pleasant change from previous spirit flights I’ve taken. Highly recommend.
Really nice, flight attendants were so helpful with me and my kids. Extremely grateful, keep up the good work and spirit :)
I liked the low price. I did not like the cramped passenger seats. As a below average size person I was cramped in the seat; I can only imagine how uncomfortable an average or large size person would be. I guess that is part of the deal with low cost airlines.
It just baffled me that spirit boarding process that I was charged 2 check in fees for a person bag and carry on. I ended up lugging 3 kids under 10 with 2 bags and to find out at the boarding area that I could not get on the plane due to my lack of reading the baggage policy. I understand if that was the case but the agent also failed to understand one item was in fact a personal item such as laptop bag and charge me as if it was a carry on not personal item. And knowing it’s a horrible storm and last flight in the destination of travel. I could have very easily handed the items to my relative to keep but I didn’t learned about this enforced policy until I was about to board.
I’m not a fan of Spirit Airlines from a not-so-good experience the last time & I swore I would not fly this airline again- bc they charge for EVERYTHING. I only flew Spirit this time bc it wasn’t my choice. I decided to use a “Mystery Ticket” bc of the great price, not knowing it would choose this airline! I found out on this trip how they pick a random seat with a “sticker” for a prize-are we in first grade? just doesn’t seem right & now the first 3 or 4 rows get special treatment-we all paid for our tickets, not just them.
The flight was delayed, and we waited for more than an hour on the plane.
This was the best spirit airlines fight I have ever had. I take spirit up to 3 or more times a year and I am ready to be the Jared of spirit. 🤪 Best flight ever. Everyone was great. I hope my return flight is the same. When you're traveling with a 9 month old you need a different type of care and accommodation. I didn't ask the staff for anything but I didn't have any added stress.
Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.
Airline changed the gate from Terminal A to Terminal D which is quite far and only sent a text message few minutes before boarding. Around 50 people missed their flight and as plane didn’t wait for them.
The personal at boarding are rude and try to steel people with their rule of personal item , really bad experience for us
I did not like that people are purposely split ip who book at the same time because we didn’t buy seats. No other airline does that.
I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.
Horrible my trip was delayed 3 hours, we already have set in the plane and they delayed the flight.
Checking in was easy and simple, crew was nice and efficient, but I would improve seat assignment randomness to make it easier to sit together based on when you check in. Overall would fly with them again.
Connecting from an international flight in Miami was horrible. We had to take check luggage on the way out go to the frontier counter and there was no one there to receive it for our domestic connecting flight we almost missed the flight because they had no Personnel on site
I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.
It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.
| Average price | Average duration | |
|---|---|---|
| Flights | $444 | 3h 05m |
| Trains | $249 | 46h 29m |