
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $99 (CheapOair) |
One-way from | $45 (Frontier) |
Popular in | December |
Cheapest in | September |
Average price | $318 |
Good round-trip deal | $160 or less |
Good one-way deal | $104 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 4/25
3:45 pm-7:40 pm
Nonstop2h 55m
Miami
Wed 4/29
3:00 pm-9:50 pm
1 stop7h 50m
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 4/28
12:50 pm-9:10 pm
2 stops7h 20m
Miami
Fri 5/1
7:15 pm-11:30 pm
1 stop5h 15m
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Mon 4/27
5:21 pm-12:54 am
1 stop6h 33m
Miami
Sat 5/2
6:00 am-10:14 am
1 stop5h 14m
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sat 5/23
3:45 pm-7:40 pm
Nonstop2h 55m
Miami
Tue 5/26
6:20 pm-10:15 pm
1 stop4h 55m
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Sun 5/3
6:45 pm-10:45 pm
Nonstop3h 00m
Miami
Sun 5/10
6:45 am-8:55 am
Nonstop3h 10m
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Tue 5/5
12:45 pm-9:55 pm
2 stops8h 10m
Miami
Tue 5/12
6:15 am-11:40 am
1 stop6h 25m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sat 5/16
6:05 pm-12:43 am
1 stop5h 38m
Miami
Sat 5/23
7:39 pm-12:07 am
1 stop5h 28m
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Wed 4/15
9:40 am-6:20 pm
2 stops7h 40m
Miami
Sat 4/18
6:15 am-10:45 am
1 stop5h 30m
ChicagoMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 4/22
5:55 am-9:10 pm
2 stops14h 15m
Miami
Sat 4/25
6:35 am-3:30 pm
2 stops9h 55m
ChicagoMiami
MDW - MIA
MDWMIA
Chicago Midway
Mon 4/20
10:00 am-6:25 pm
2 stops7h 25m
Miami
Wed 4/22
7:00 am-12:00 pm
2 stops6h 00m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
Booking 41 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Miami. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, October is the cheapest month in which you can book a flight from Chicago to Miami (average of $49). Flying from Chicago to Miami in July is currently the most expensive (average of $118). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
When flying from Chicago to Miami, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 28% versus a flight in the morning.
Travelers seeking maximum savings on their Chicago to Miami flight should consider departing on Wednesday at noon when fares are most often at their lowest. Wednesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to MIA are scheduled on a Monday (60 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (38 on average).
About 17% of weekly flights between Chicago and Miami have experienced delays in the past year, with the average delay time being 147 minutes.
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Over the last year, United Airlines have had the lowest number of delays on this route, with just 15% of flights being delayed.
Comfort
Food
Boarding
Entertainment
Overall
Crew
Reviews
Scott,Feb 2026
HOU - FLL
Comfort
Food
Boarding
Entertainment
Overall
Crew
Reviews
Scott,Feb 2026
HOU - FLL
Comfort
Food
Boarding
Entertainment
Overall
Crew
Reviews
Scott,Feb 2026
HOU - FLL
Comfort
Food
Boarding
Entertainment
Overall
Crew
Reviews
Scott,Feb 2026
HOU - FLL
Comfort
Food
Boarding
Entertainment
Overall
Crew
Reviews
Scott,Feb 2026
HOU - FLL
Comfort
Food
Boarding
Entertainment
Overall
Crew
Reviews
Scott,Feb 2026
HOU - FLL
Oh, Miami. Some like it hot, and when they do, they go to Miami, Florida. Chicago residents looking to escape the harsh Midwest winter or spice things up for the summer are bound to find Miami an accommodating getaway. From the beaches to the museums, and the rich Cuban-influenced culture to the culinary delights, Miami has a little something for everyone. Lodging options are aplenty as well for those leaving the Windy City for Miami. Stay in an exotic luxury hotel along the water, book a condo at a golf resort, or stay frugal at a modestly priced hotel. Whichever you choose, make sure your location accommodates your recreation plans if you're not renting a car.
While Chicago is known for its windy weather and down-to-earth residents, Miami likes to kick things up a notch with both its subtropical climate and appreciation for all things caliente. For most of the year, you can leave your hat, gloves and heavy coat in Chi-Town when you depart for Miami; instead, bring some sunscreen.
Looking for a hot time in the city or relaxed sunbathing at the beach? Use our smart search engine to find the best deals on flights from Chicago to Miami.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$215 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$70 | Average$183 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$89 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$367 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$134 | Average$357 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$165 | Average$358 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$176 | Average$249 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$199 | Average$392 | FlexibilityNo cancel fee | On-time63% |