Cheap Flights from Chicago to Jacksonville
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Deals from
Chicago
RatePunk searches hundreds of travel sites at once for deals on flights to Jacksonville
Prices updated 24 days ago
486,190 searches this week
171 airlines compared
80%+ AI score for best value
Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)
Today’s best flight deals from Chicago to Jacksonville
Explore current cheapest deals departing from Chicago to Jacksonville
Round trip
Sort by: Cheapest
September 15 - September 30
MDW - Jacksonville
$247
$172
Round trip
September 29 - September 30
MDW - Jacksonville
$296
$172
Round trip
September 22 - September 30
MDW - Jacksonville
$275
$172
Round trip
September 21 - September 30
MDW - Jacksonville
$273
$173
Round trip
September 22 - October 4
MDW - Jacksonville
$258
$180
Round trip
September 22 - October 11
MDW - Jacksonville
$250
$181
Round trip
September 15 - October 12
MDW - Jacksonville
$243
$181
Round trip
September 29 - October 12
MDW - Jacksonville
$264
$181
Round trip
September 15 - October 11
MDW - Jacksonville
$243
$181
Round trip
September 15 - September 21
MDW - Jacksonville
$279
$182
Round trip
Unlock all 500+ flight deals to Jacksonville and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Chicago to Jacksonville
How much is a round trip from Chicago to Jacksonville
Regular price: $205 - $351
Prices are currently below the regular range for flights from Chicago to Jacksonville.
The regular price range for this route is typically between $205 and $351. The current lowest deal is $172 with Frontier Airlines, for travel from September 15 to September 30.
now $172
Low $205
High $351
The cheapest time to fly from Chicago to Jacksonville
The cheapest month to fly from Chicago to Jacksonville is January, with a median price of $211. The most expensive month is March, with a median price of $426. Prices are generally lower from January to December.
January
Flights from $211
March
Flights from $426
Direct flights from Chicago to Jacksonville
American Airlines
Last-minute flights going from Chicago to Jacksonville
Thu, Jun 18
ORD - Jacksonville
Chicago (ORD) - Jacksonville (JAX)
Deutsche Luft Hansa
$509
$486
One-way
Fri, Jun 19
ORD - Jacksonville
Chicago (ORD) - Jacksonville (JAX)
Frontier Airlines
$499
$326
One-way
Wed, Jul 1
MDW - Jacksonville
Chicago (MDW) - Jacksonville (JAX)
Frontier Airlines
$374
$246
One-way
Thu, Jul 2
RFD - Jacksonville
Chicago (RFD) - Jacksonville (JAX)
Allegiant Air
$329
$270
One-way
Thu, Jul 2
RFD - Jacksonville
Chicago (RFD) - Jacksonville (JAX)
Allegiant Air
$361
$292
One-way
Fri, Jul 3
MDW - Jacksonville
Chicago (MDW) - Jacksonville (JAX)
Southwest Airlines
$384
$301
One-way
Biggest price drops on these dates for flights from Chicago to Jacksonville
Nov 24 - Nov 30
$602 → $378
37%
Nov 25 - Nov 28
$616 → $398
35%
Nov 21 - Nov 30
$596 → $402
33%
Nov 20 - Nov 30
$581 → $402
31%
Popular Airports to fly from Chicago to Jacksonville
Chicago - Jacksonville route insights
💸 Price insights
Recent fares are above the typical level.
Recent fares from Chicago to Jacksonville are above the typical level, with a median price of $277.
📅 Best time to fly
January is historically the cheapest month to fly.
Historically, January is the cheapest month to fly from Chicago to Jacksonville, with a median price of $211.
⏱️ Flight duration
Flights are typically 10h 35m long.
Flights from Chicago to Jacksonville typically take 10 hours and 35 minutes, including layovers.
✈️ Airlines & availability
Connecting flights are more common.
About 33% of recent deals are for direct flights. Connecting flights typically have 2 stopovers.
🏆 Airline highlight
American Airlines offers direct flights.
American Airlines is one of the carriers that historically offers direct flights on this route.
🎯 Booking tip
Deals appear frequently for this route.
Historically, deals for flights from Chicago to Jacksonville appear frequently, about once per day.
Chicago main airports to depart from
Chicago Midway International (MDW)
Consider Chicago Midway International for flights from Chicago to Jacksonville, often offering competitive prices.
📍 ~15 km from Chicago (reachable by car)
💸 Flights from ~$172
Chicago Rockford International (RFD)
Chicago Rockford International is an alternative departure airport for your trip to Jacksonville.
📍 ~120 km from Chicago (reachable by car)
💸 Flights from ~$194
O Hare International (ORD)
O Hare International is a major departure option for flights from Chicago to Jacksonville.
📍 ~25 km from Chicago (reachable by car or train)
💸 Flights from ~$182
Jacksonville main airports to arrive at
Jacksonville International (JAX)
Jacksonville International Airport is a convenient arrival option for flights from Chicago to Jacksonville.
📍 ~20 km from Jacksonville (reachable by car)
💸 Flights from ~$172
Airports nearby Jacksonville used as alternative
Orlando International (MCO)
Orlando International is a major international hub with significantly more direct flight options and competitive pricing.
📍 ~180 km from Jacksonville (reachable by car)
💸 Flights from ~$97
Orlando Sanford International (SFB)
Orlando Sanford International is a primary hub for low-cost carriers, often providing much cheaper point-to-point domestic flights.
📍 ~170 km from Jacksonville (reachable by car)
💸 Flights from ~$85
Savannah/Hilton Head International (SAV)
Savannah/Hilton Head International is a reliable regional alternative with good domestic connectivity through major US carriers.
📍 ~200 km from Jacksonville (reachable by car)
💸 Flights from ~$186
Daytona Beach International (DAB)
Daytona Beach International is a relatively close alternative for major carriers with very low stress and quick transit.
📍 ~140 km from Jacksonville (reachable by car)
💸 Flights from ~$316
Gainesville Regional (GNV)
Gainesville Regional is the closest alternative airport geographically, useful for regional connections.
📍 ~100 km from Jacksonville (reachable by car)
💸 Flights from ~$398
Business & First Class Flight Deals to Jacksonville
Discover luxury on the budget with premium cabin class on flights from Chicago to Jacksonville.
Elite
Best Elite deals to Jacksonville
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From ORD
Elite
Aug 01
Jacksonville, United States
82% AI deal score
$1,050
$569
Save $481
From ORD
Elite
Aug 11
Jacksonville, United States
80% AI deal score
$774
$497
Save $277
From ORD
Elite
Aug 19
Jacksonville, United States
80% AI deal score
$790
$497
Save $293
From ORD
Elite
Jul 22
Jacksonville, United States
80% AI deal score
$760
$497
Save $263
From ORD
Elite
Aug 04
Jacksonville, United States
80% AI deal score
$875
$545
Save $330
From ORD
Elite
Aug 13
Jacksonville, United States
80% AI deal score
$930
$548
Save $382
From ORD
Elite
Jul 07
Jacksonville, United States
79% AI deal score
$736
$497
Save $239
From ORD
Elite
Jul 15
Jacksonville, United States
79% AI deal score
$711
$497
Save $214
From ORD
Elite
Aug 11
Jacksonville, United States
79% AI deal score
$844
$546
Save $298
From ORD
Elite
Jul 22
Jacksonville, United States
79% AI deal score
$906
$569
Save $337
From ORD
Elite
Jul 29
Jacksonville, United States
79% AI deal score
$883
$569
Save $314
From ORD
Elite
Jul 20
Jacksonville, United States
79% AI deal score
$918
$569
Save $349
From ORD
Elite
Aug 07
Jacksonville, United States
79% AI deal score
$1,010
$618
Save $392
From ORD
Elite
Jul 31
Jacksonville, United States
78% AI deal score
$848
$569
Save $279
From ORD
Elite
Jul 15
Jacksonville, United States
78% AI deal score
$830
$569
Save $261
From ORD
Elite
Aug 13
Jacksonville, United States
77% AI deal score
$832
$595
Save $237
From ORD
Elite
Jul 11
Jacksonville, United States
77% AI deal score
$899
$606
Save $293
From ORD
Elite
Jul 13
Jacksonville, United States
77% AI deal score
$917
$617
Save $300
From ORD
Elite
Jul 10
Jacksonville, United States
77% AI deal score
$903
$617
Save $286
From ORD
Elite
Jul 07
Jacksonville, United States
77% AI deal score
$929
$617
Save $312
From ORD
Elite
Aug 03
Jacksonville, United States
77% AI deal score
$869
$618
Save $251
From ORD
Elite
Aug 01
Jacksonville, United States
77% AI deal score
$868
$618
Save $250
From ORD
Elite
Jul 28
Jacksonville, United States
76% AI deal score
$738
$569
Save $169
From ORD
Elite
Oct 24
Jacksonville, United States
76% AI deal score
$811
$595
Save $216
From ORD
Elite
Jul 29
Jacksonville, United States
76% AI deal score
$858
$607
Save $251
From ORD
Elite
Sep 21
Jacksonville, United States
75% AI deal score
$766
$595
Save $171
From ORD
Elite
Jul 15
Jacksonville, United States
75% AI deal score
$653
$525
Save $128
From ORD
Elite
Jul 10
Jacksonville, United States
70% AI deal score
$747
$617
Save $130
From ORD
Elite
Sep 07
Jacksonville, United States
70% AI deal score
$752
$618
Save $134
From ORD
Elite
Jul 30
Jacksonville, United States
70% AI deal score
$739
$618
Save $121
From ORD
Elite
Jul 08
Jacksonville, United States
70% AI deal score
$641
$525
Save $116
From ORD
Elite
Oct 21
Jacksonville, United States
70% AI deal score
$792
$574
Save $218
From ORD
Elite
Sep 28
Jacksonville, United States
70% AI deal score
$864
$623
Save $241
From ORD
Elite
Dec 05
Jacksonville, United States
69% AI deal score
$663
$574
Save $89
From ORD
Elite
Nov 05
Jacksonville, United States
69% AI deal score
$793
$646
Save $147
From ORD
Elite
Aug 12
Jacksonville, United States
68% AI deal score
$780
$635
Save $145
From ORD
Elite
Aug 10
Jacksonville, United States
68% AI deal score
$781
$646
Save $135
From ORD
Elite
Aug 02
Jacksonville, United States
67% AI deal score
$776
$684
Save $92
From ORD
Elite
Oct 22
Jacksonville, United States
67% AI deal score
$798
$684
Save $114
From ORD
Elite
Nov 19
Jacksonville, United States
67% AI deal score
$793
$707
Save $86
From ORD
Elite
Jun 23
Jacksonville, United States
67% AI deal score
$796
$729
Save $67
From ORD
Elite
Jul 31
Jacksonville, United States
66% AI deal score
$645
$597
Save $48
From ORD
Elite
Jul 15
Jacksonville, United States
66% AI deal score
$640
$597
Save $43
From ORD
Elite
Aug 01
Jacksonville, United States
66% AI deal score
$782
$692
Save $90
From ORD
Elite
Nov 21
Jacksonville, United States
66% AI deal score
$777
$706
Save $71
From ORD
Elite
Jul 15
Jacksonville, United States
65% AI deal score
$638
$615
Save $23
From ORD
Elite
Nov 26
Jacksonville, United States
50% AI deal score
$829
$809
Save $20
From ORD
Elite
Nov 01
Jacksonville, United States
50% AI deal score
$833
$809
Save $24
From ORD
Elite
Jul 07
Jacksonville, United States
49% AI deal score
$639
$634
Save $5
From ORD
Elite
Jul 20
Jacksonville, United States
49% AI deal score
$647
$635
Save $12
From ORD
Elite
Jul 13
Jacksonville, United States
49% AI deal score
$652
$645
Save $7
From ORD
Elite
Jul 17
Jacksonville, United States
49% AI deal score
$669
From ORD
Elite
Jul 17
Jacksonville, United States
49% AI deal score
$669
From ORD
Elite
Jul 18
Jacksonville, United States
49% AI deal score
$669
From ORD
Elite
Jul 22
Jacksonville, United States
49% AI deal score
$692
From ORD
Elite
Jul 23
Jacksonville, United States
49% AI deal score
$707
From ORD
Elite
Jul 06
Jacksonville, United States
49% AI deal score
$717
From ORD
Elite
Jul 13
Jacksonville, United States
49% AI deal score
$717
From ORD
Elite
Jul 19
Jacksonville, United States
49% AI deal score
$730
From ORD
Elite
Nov 19
Jacksonville, United States
49% AI deal score
$847
From ORD
Elite
Oct 29
Jacksonville, United States
41% AI deal score
$1,114
From ORD
Elite
Nov 17
Jacksonville, United States
41% AI deal score
$1,114
From ORD
Elite
Dec 01
Jacksonville, United States
41% AI deal score
$1,114
From ORD
Elite
Dec 05
Jacksonville, United States
41% AI deal score
$1,114
From ORD
Elite
Nov 20
Jacksonville, United States
40% AI deal score
$1,154
From ORD
Elite
Dec 02
Jacksonville, United States
38% AI deal score
$1,419
From ORD
Elite
Nov 08
Jacksonville, United States
38% AI deal score
$1,419
From ORD
Elite
Nov 04
Jacksonville, United States
38% AI deal score
$1,419
From ORD
Elite
Jul 10
Jacksonville, United States
37% AI deal score
$3,665
From ORD
Elite
Jul 10
Jacksonville, United States
37% AI deal score
$3,679
From ORD
Elite
Aug 28
Jacksonville, United States
37% AI deal score
$3,707
From ORD
Elite
Aug 28
Jacksonville, United States
37% AI deal score
$3,720
From ORD
Elite
Jul 10
Jacksonville, United States
37% AI deal score
$3,738
From ORD
Elite
Jul 10
Jacksonville, United States
37% AI deal score
$3,745
From ORD
Elite
Jul 10
Jacksonville, United States
37% AI deal score
$3,745
From ORD
Elite
Jul 24
Jacksonville, United States
37% AI deal score
$3,789
From ORD
Elite
Jul 20
Jacksonville, United States
37% AI deal score
$3,808
From ORD
Elite
Jul 24
Jacksonville, United States
37% AI deal score
$3,812
From ORD
Elite
Jul 24
Jacksonville, United States
37% AI deal score
$3,814
From ORD
Elite
Jul 31
Jacksonville, United States
37% AI deal score
$3,817
From ORD
Elite
Jul 31
Jacksonville, United States
37% AI deal score
$3,819
From ORD
Elite
Jul 24
Jacksonville, United States
37% AI deal score
$3,826
From ORD
Elite
Jul 31
Jacksonville, United States
37% AI deal score
$3,832
From ORD
Elite
Jul 24
Jacksonville, United States
37% AI deal score
$3,834
From ORD
Elite
Jul 31
Jacksonville, United States
37% AI deal score
$3,840
From ORD
Elite
Jul 24
Jacksonville, United States
37% AI deal score
$3,842
From ORD
Elite
Jul 31
Jacksonville, United States
37% AI deal score
$3,843
From ORD
Elite
Jul 30
Jacksonville, United States
37% AI deal score
$3,843
From ORD
Elite
Jul 30
Jacksonville, United States
37% AI deal score
$3,845
From ORD
Elite
Jul 10
Jacksonville, United States
37% AI deal score
$3,848
From ORD
Elite
Jul 10
Jacksonville, United States
37% AI deal score
$3,853
From ORD
Elite
Jul 30
Jacksonville, United States
37% AI deal score
$3,857
From ORD
Elite
Jul 24
Jacksonville, United States
37% AI deal score
$3,862
From ORD
Elite
Jul 30
Jacksonville, United States
37% AI deal score
$3,866
From ORD
Elite
Jul 31
Jacksonville, United States
37% AI deal score
$3,867
From ORD
Elite
Jul 30
Jacksonville, United States
37% AI deal score
$3,868
From ORD
Elite
Jul 10
Jacksonville, United States
37% AI deal score
$3,871
From ORD
Elite
Aug 14
Jacksonville, United States
37% AI deal score
$3,875
From ORD
Elite
Jul 10
Jacksonville, United States
37% AI deal score
$3,879
From ORD
Elite
Jul 24
Jacksonville, United States
37% AI deal score
$3,881