Find cheap flights from Chicago to Destin

CHI - DSI

Find cheap flights from Chicago to Destin

Search hundreds of travel sites at once for deals on flights to Destin

Round-trip
Economy
Chicago (CHI)
Destin
Sat 5/15
Sat 5/22
Any month
Compare vs. KAYAK |

Good to know

Low season

SeptemberBest time to beat the crowds with an average 22% drop in price.

High season

DecemberMost popular time to fly with an average 36% increase in price.

Average price round-trip

$362(avg. price over the last 2 weeks)

Good deal round-trip

$279or less

Good deal one-way

$176or less

When to book flights from Chicago to Destin

Estimated round-trip price
Average price per month

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $176 or less one-way and $279 or less round-trip.
  • High season is considered to be November, December and January. The cheapest month to fly is September.
  • Morning departure is around 254% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking flights from Chicago to Destin

Are there Destin travel restrictions currently due to Coronavirus?

How long does a flight from Chicago to Destin take?

Which airlines provide the cheapest flights from Chicago to Destin?

Do I need a passport to fly between Chicago and Destin?

Which airports will I be using when flying from Chicago to Destin?

How does KAYAK find such low prices on flights from Chicago to Destin?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Destin?

What is the Hacker Fare option on flights from Chicago to Destin?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Destin?

COVID-19 information

Safety measures for airlines flying from Chicago to Destin

Airlines flying from Chicago to Destin have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago to Destin

Mandatory masks

Masks required on board, masks provided on flights from Chicago to Destin

Social distancing seating

Middle seats unavailable to book on flights from Chicago to Destin

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago to Destin

Book cheap flights from Chicago to Destin

Recent round-trip flight deals

7/15
Thu
1 stop
Multiple Airlines
22h 05m
ORD - DSI
7/18
Sun
1 stop
Multiple Airlines
23h 42m
DSI - ORD
9/23
Thu
1 stop
Multiple Airlines
22h 15m
ORD - DSI
9/26
Sun
1 stop
Multiple Airlines
24h 24m
DSI - ORD
8/5
Thu
1 stop
Multiple Airlines
22h 55m
ORD - DSI
8/8
Sun
1 stop
Multiple Airlines
23h 42m
DSI - ORD
9/9
Thu
1 stop
Multiple Airlines
22h 15m
ORD - DSI
9/12
Sun
1 stop
Multiple Airlines
24h 24m
DSI - ORD
8/26
Thu
1 stop
Multiple Airlines
22h 15m
ORD - DSI
8/29
Sun
1 stop
Multiple Airlines
17h 48m
DSI - ORD
8/11
Wed
2 stops
Multiple Airlines
45h 09m
ORD - DSI
8/15
Sun
1 stop
Multiple Airlines
7h 32m
DSI - ORD
7/15
Thu
2 stops
Multiple Airlines
21h 20m
ORD - DSI
7/18
Sun
1 stop
Multiple Airlines
23h 42m
DSI - ORD
9/23
Thu
2 stops
Multiple Airlines
21h 50m
ORD - DSI
9/26
Sun
1 stop
Multiple Airlines
24h 24m
DSI - ORD
9/9
Thu
2 stops
Multiple Airlines
21h 50m
ORD - DSI
9/12
Sun
1 stop
Multiple Airlines
24h 24m
DSI - ORD
9/9
Thu
1 stop
Multiple Airlines
22h 15m
ORD - DSI
9/12
Sun
2 stops
Multiple Airlines
16h 54m
DSI - ORD
7/21
Wed
3 stops
Multiple Airlines
44h 05m
ORD - DSI
7/25
Sun
1 stop
Multiple Airlines
7h 32m
DSI - ORD
8/5
Thu
2 stops
Multiple Airlines
21h 15m
ORD - DSI
8/8
Sun
1 stop
Multiple Airlines
7h 32m
DSI - ORD
8/26
Thu
2 stops
Multiple Airlines
21h 40m
ORD - DSI
8/29
Sun
1 stop
Multiple Airlines
7h 32m
DSI - ORD
7/21
Wed
2 stops
Multiple Airlines
44h 13m
ORD - DSI
7/25
Sun
1 stop
Multiple Airlines
7h 32m
DSI - ORD
7/15
Thu
3 stops
Multiple Airlines
19h 27m
ORD - DSI
7/18
Sun
1 stop
Multiple Airlines
23h 42m
DSI - ORD
9/9
Thu
2 stops
Multiple Airlines
21h 18m
ORD - DSI
9/12
Sun
2 stops
Multiple Airlines
16h 54m
DSI - ORD
7/15
Thu
2 stops
Multiple Airlines
34h 05m
ORD - DSI
7/18
Sun
3 stops
Multiple Airlines
29h 33m
DSI - ORD
9/9
Thu
2 stops
Multiple Airlines
17h 36m
ORD - DSI
9/12
Sun
2 stops
Multiple Airlines
16h 54m
DSI - ORD
9/23
Thu
2 stops
Multiple Airlines
21h 50m
ORD - DSI
9/26
Sun
2 stops
Multiple Airlines
16h 54m
DSI - ORD
7/15
Thu
3 stops
Multiple Airlines
30h 00m
ORD - DSI
7/18
Sun
3 stops
Multiple Airlines
29h 33m
DSI - ORD
Show more results

Recent one-way flight deals

5/22
Sat
2 stops
Multiple Airlines
27h 21m
ORD - DSI
5/28
Fri
2 stops
Multiple Airlines
43h 05m
ORD - DSI
5/28
Fri
3 stops
Multiple Airlines
42h 55m
ORD - DSI
8/1
Sun
2 stops
Linear Air Taxi
17h 56m
ORD - DSI
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