Cheap Flights from Jacksonville to Chicago
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Deals from
Jacksonville
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
Prices updated 24 days ago
486,190 searches this week
171 airlines compared
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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 Jacksonville to Chicago
Explore current cheapest deals departing from Jacksonville to Chicago
Round trip
Sort by: Cheapest
September 23 - October 13
JAX - Chicago
$286
$179
Round trip
September 23 - September 29
JAX - Chicago
$325
$179
Round trip
September 23 - October 6
JAX - Chicago
$295
$179
Round trip
September 22 - October 13
JAX - Chicago
$286
$183
Round trip
September 22 - September 29
JAX - Chicago
$325
$183
Round trip
September 22 - October 6
JAX - Chicago
$295
$183
Round trip
September 30 - October 13
JAX - Chicago
$307
$185
Round trip
September 30 - October 6
JAX - Chicago
$336
$185
Round trip
July 7 - July 8
JAX - Chicago
$184
$197
Round trip
July 21 - July 28
JAX - Chicago
$169
$197
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Jacksonville to Chicago
How much is a round trip from Jacksonville to Chicago
Regular price: $240 - $346
Prices for flights from Jacksonville to Chicago are currently below the regular range.
The regular price range for flights from Jacksonville to Chicago is between $240 and $346. The current lowest deal is $179 with Frontier Airlines for travel from Sep 23-Oct 13.
now $179
Low $240
High $346
The cheapest time to fly from Jacksonville to Chicago
The cheapest month to fly from Jacksonville to Chicago is February, with a median price of $191. The most expensive month is March, with a median price of $613. Prices are generally lower from January to December.
February
Flights from $191
March
Flights from $613
Direct flights from Jacksonville to Chicago
United Airlines
Last-minute flights going from Jacksonville to Chicago
Tue, Jun 16
JAX - Chicago
Jacksonville (JAX) - Chicago (MDW)
Frontier Airlines
$472
$290
One-way
Wed, Jun 17
JAX - Chicago
Jacksonville (JAX) - Chicago (MDW)
Frontier Airlines
$397
$295
One-way
Fri, Jun 19
JAX - Chicago
Jacksonville (JAX) - Chicago (MDW)
Frontier Airlines
$468
$343
One-way
Tue, Jun 23
JAX - Chicago
Jacksonville (JAX) - Chicago (MDW)
Frontier Airlines
$360
$273
One-way
Wed, Jun 24
JAX - Chicago
Jacksonville (JAX) - Chicago (MDW)
Frontier Airlines
$349
$273
One-way
Wed, Jun 24
JAX - Chicago
Jacksonville (JAX) - Chicago (MDW)
Frontier Airlines
$384
$291
One-way
Biggest price drops on these dates for flights from Jacksonville to Chicago
Jun 16 - Jun 17
$472 → $290
39%
Aug 13 - Aug 16
$396 → $218
45%
Aug 14 - Aug 19
$392 → $220
44%
Aug 26 - Aug 30
$397 → $229
42%
Popular Airports to fly from Jacksonville to Chicago
Jacksonville - Chicago route insights
💸 Price insights
Recent fares are above the typical level
Recent fares for flights from Jacksonville to Chicago are above the typical level at $179.
📅 Best time to fly
February is historically cheapest at $191
Historically, February is the cheapest month to fly from Jacksonville to Chicago, with a median price of $191.
⏱️ Flight duration
Typical flight time is 6h 1m
The typical flight duration from Jacksonville to Chicago is 6 hours and 1 minute.
✈️ Airlines & availability
Mixed availability of direct flights
About 46% of recent deals are for direct flights. Connecting flights typically have 2 stopovers.
🏆 Airline highlight
United Airlines offers direct flights
United Airlines is one of the carriers that offers direct flights on the Jacksonville to Chicago route.
🎯 Booking tip
Deals appear frequently
Deals for flights from Jacksonville to Chicago appear frequently, with over 1 deal per day.
Jacksonville main airports to depart from
Jacksonville International (JAX)
Jacksonville International is the cheapest option for flights from Jacksonville to Chicago.
📍 ~20 km from Jacksonville (reachable by car)
💸 Flights from ~$179
Chicago main airports to arrive at
Chicago Midway International (MDW)
Chicago Midway International is a good choice for flights from Jacksonville to Chicago, with prices from $179.
📍 ~15 km from Chicago city center (reachable by car or public transport)
💸 Flights from ~$179
Chicago Rockford International (RFD)
Chicago Rockford International is an option for flights from Jacksonville to Chicago.
📍 ~120 km from Chicago city center (reachable by car)
💸 Flights from ~$194
O Hare International (ORD)
O Hare International is an option for flights from Jacksonville to Chicago.
📍 ~40 km from Chicago city center (reachable by car or public transport)
💸 Flights from ~$191
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers excellent proximity to Chicago with high-frequency flight options and direct rail access.
📍 ~135 km from Chicago (reachable by rail)
💸 Flights from ~$333
South Bend International (SBN)
South Bend International is the closest alternative to Chicago, with direct commuter rail access to downtown.
📍 ~130 km from Chicago (reachable by rail)
💸 Flights from ~$204
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub, offering a wide range of cabin classes for travelers.
📍 ~230 km from Chicago (reachable by car)
💸 Flights from ~$73
Dane County Regional (MSN)
Dane County Regional is a reliable regional airport with consistent service levels and less congestion.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$240
Fort Wayne International (FWA)
Fort Wayne International provides stable regional service and is an alternative for southeastern Chicago suburbs.
📍 ~250 km from Chicago (reachable by car)
💸 Flights from ~$237
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Jacksonville to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From JAX
Elite
Sep 26
Chicago, United States
82% AI deal score
$1,405
$556
Save $849
From JAX
Elite
Aug 11
Chicago, United States
81% AI deal score
$799
$497
Save $302
From JAX
Elite
Aug 25
Chicago, United States
80% AI deal score
$788
$497
Save $291
From JAX
Elite
Jul 14
Chicago, United States
80% AI deal score
$730
$497
Save $233
From JAX
Elite
Jul 15
Chicago, United States
80% AI deal score
$730
$497
Save $233
From JAX
Elite
Jul 21
Chicago, United States
80% AI deal score
$735
$497
Save $238
From JAX
Elite
Aug 15
Chicago, United States
80% AI deal score
$875
$546
Save $329
From JAX
Elite
Sep 23
Chicago, United States
80% AI deal score
$1,128
$597
Save $531
From JAX
Elite
Aug 22
Chicago, United States
80% AI deal score
$1,410
$646
Save $764
From JAX
Elite
Oct 03
Chicago, United States
80% AI deal score
$1,340
$646
Save $694
From JAX
Elite
Jul 28
Chicago, United States
79% AI deal score
$720
$497
Save $223
From JAX
Elite
Nov 14
Chicago, United States
79% AI deal score
$828
$546
Save $282
From JAX
Elite
Aug 29
Chicago, United States
79% AI deal score
$853
$546
Save $307
From JAX
Elite
Aug 19
Chicago, United States
79% AI deal score
$841
$546
Save $295
From JAX
Elite
Aug 04
Chicago, United States
79% AI deal score
$815
$546
Save $269
From JAX
Elite
Aug 26
Chicago, United States
79% AI deal score
$884
$569
Save $315
From JAX
Elite
Jul 27
Chicago, United States
78% AI deal score
$803
$569
Save $234
From JAX
Elite
Oct 04
Chicago, United States
78% AI deal score
$1,380
$707
Save $673
From JAX
Elite
Dec 12
Chicago, United States
78% AI deal score
$1,369
$718
Save $651
From JAX
Elite
Sep 10
Chicago, United States
78% AI deal score
$1,402
$727
Save $675
From JAX
Elite
Aug 15
Chicago, United States
77% AI deal score
$756
$546
Save $210
From JAX
Elite
Aug 15
Chicago, United States
77% AI deal score
$754
$546
Save $208
From JAX
Elite
Jul 30
Chicago, United States
77% AI deal score
$755
$569
Save $186
From JAX
Elite
Jul 29
Chicago, United States
77% AI deal score
$792
$569
Save $223
From JAX
Elite
Jul 28
Chicago, United States
77% AI deal score
$792
$569
Save $223
From JAX
Elite
Jul 29
Chicago, United States
77% AI deal score
$756
$569
Save $187
From JAX
Elite
Jul 24
Chicago, United States
77% AI deal score
$781
$569
Save $212
From JAX
Elite
Aug 17
Chicago, United States
77% AI deal score
$832
$595
Save $237
From JAX
Elite
Aug 20
Chicago, United States
77% AI deal score
$864
$595
Save $269
From JAX
Elite
Jul 14
Chicago, United States
76% AI deal score
$726
$569
Save $157
From JAX
Elite
Jul 21
Chicago, United States
76% AI deal score
$730
$569
Save $161
From JAX
Elite
Jul 29
Chicago, United States
76% AI deal score
$720
$569
Save $151
From JAX
Elite
Jul 20
Chicago, United States
76% AI deal score
$726
$569
Save $157
From JAX
Elite
Jun 30
Chicago, United States
76% AI deal score
$754
$586
Save $168
From JAX
Elite
Aug 15
Chicago, United States
76% AI deal score
$798
$595
Save $203
From JAX
Elite
Aug 20
Chicago, United States
76% AI deal score
$788
$595
Save $193
From JAX
Elite
Sep 26
Chicago, United States
76% AI deal score
$779
$595
Save $184
From JAX
Elite
Oct 03
Chicago, United States
76% AI deal score
$1,380
$605
Save $775
From JAX
Elite
Jun 24
Chicago, United States
76% AI deal score
$804
$634
Save $170
From JAX
Elite
Sep 23
Chicago, United States
75% AI deal score
$772
$525
Save $247
From JAX
Elite
Jul 07
Chicago, United States
75% AI deal score
$651
$525
Save $126
From JAX
Elite
Aug 19
Chicago, United States
75% AI deal score
$840
$574
Save $266
From JAX
Elite
Aug 22
Chicago, United States
72% AI deal score
$856
$574
Save $282
From JAX
Elite
Oct 03
Chicago, United States
71% AI deal score
$759
$595
Save $164
From JAX
Elite
Jul 14
Chicago, United States
71% AI deal score
$640
$525
Save $115
From JAX
Elite
Sep 19
Chicago, United States
70% AI deal score
$789
$574
Save $215
From JAX
Elite
Oct 27
Chicago, United States
70% AI deal score
$797
$597
Save $200
From JAX
Elite
Aug 20
Chicago, United States
70% AI deal score
$856
$623
Save $233
From JAX
Elite
Jun 29
Chicago, United States
69% AI deal score
$746
$659
Save $87
From JAX
Elite
Aug 27
Chicago, United States
69% AI deal score
$860
$684
Save $176
From JAX
Elite
Nov 14
Chicago, United States
68% AI deal score
$682
$574
Save $108
From JAX
Elite
Nov 05
Chicago, United States
68% AI deal score
$684
$574
Save $110
From JAX
Elite
Oct 09
Chicago, United States
68% AI deal score
$777
$635
Save $142
From JAX
Elite
Oct 03
Chicago, United States
68% AI deal score
$765
$646
Save $119
From JAX
Elite
Sep 18
Chicago, United States
68% AI deal score
$810
$646
Save $164
From JAX
Elite
Jun 30
Chicago, United States
67% AI deal score
$814
$675
Save $139
From JAX
Elite
Nov 07
Chicago, United States
67% AI deal score
$779
$702
Save $77
From JAX
Elite
Jul 24
Chicago, United States
67% AI deal score
$643
$597
Save $46
From JAX
Elite
Oct 15
Chicago, United States
67% AI deal score
$791
$684
Save $107
From JAX
Elite
Jun 26
Chicago, United States
66% AI deal score
$1,376
$1,059
Save $317
From JAX
Elite
Nov 05
Chicago, United States
66% AI deal score
$688
$623
Save $65
From JAX
Elite
Jun 27
Chicago, United States
65% AI deal score
$906
$762
Save $144
From JAX
Elite
Jul 19
Chicago, United States
50% AI deal score
$649
$635
Save $14
From JAX
Elite
Jul 22
Chicago, United States
50% AI deal score
$649
$635
Save $14
From JAX
Elite
Jul 08
Chicago, United States
49% AI deal score
$638
$634
Save $4
From JAX
Elite
Jul 28
Chicago, United States
49% AI deal score
$645
$635
Save $10
From JAX
Elite
Jul 12
Chicago, United States
49% AI deal score
$648
$645
Save $3
From JAX
Elite
Dec 05
Chicago, United States
49% AI deal score
$646
From JAX
Elite
Jul 20
Chicago, United States
49% AI deal score
$669
From JAX
Elite
Jul 15
Chicago, United States
49% AI deal score
$669
From JAX
Elite
Jul 20
Chicago, United States
49% AI deal score
$669
From JAX
Elite
Jul 15
Chicago, United States
49% AI deal score
$669
From JAX
Elite
Nov 05
Chicago, United States
49% AI deal score
$699
$684
Save $15
From JAX
Elite
Nov 19
Chicago, United States
48% AI deal score
$809
From JAX
Elite
Jun 26
Chicago, United States
48% AI deal score
$817
$748
Save $69
From JAX
Elite
Nov 26
Chicago, United States
42% AI deal score
$1,007
From JAX
Elite
Nov 25
Chicago, United States
42% AI deal score
$1,030
From JAX
Elite
Nov 01
Chicago, United States
42% AI deal score
$1,114
From JAX
Elite
Nov 05
Chicago, United States
42% AI deal score
$1,114
From JAX
Elite
Nov 15
Chicago, United States
41% AI deal score
$1,114
From JAX
Elite
Dec 05
Chicago, United States
41% AI deal score
$1,114
From JAX
Elite
Dec 08
Chicago, United States
41% AI deal score
$1,114
From JAX
Elite
Aug 10
Chicago, United States
40% AI deal score
$3,506
From JAX
Elite
Aug 27
Chicago, United States
40% AI deal score
$3,524
From JAX
Elite
Aug 28
Chicago, United States
40% AI deal score
$3,532
From JAX
Elite
Aug 11
Chicago, United States
40% AI deal score
$3,533
From JAX
Elite
Aug 14
Chicago, United States
40% AI deal score
$3,585
From JAX
Elite
Aug 31
Chicago, United States
40% AI deal score
$3,627
From JAX
Elite
Sep 01
Chicago, United States
40% AI deal score
$3,646
From JAX
Elite
Nov 22
Chicago, United States
40% AI deal score
$1,204
From JAX
Elite
Jul 24
Chicago, United States
39% AI deal score
$3,434
From JAX
Elite
Jul 27
Chicago, United States
39% AI deal score
$3,503
From JAX
Elite
Aug 11
Chicago, United States
39% AI deal score
$3,515
From JAX
Elite
Jul 25
Chicago, United States
39% AI deal score
$3,526
From JAX
Elite
Aug 04
Chicago, United States
39% AI deal score
$3,527
From JAX
Elite
Aug 06
Chicago, United States
39% AI deal score
$3,543
From JAX
Elite
Aug 13
Chicago, United States
39% AI deal score
$3,548
From JAX
Elite
Aug 03
Chicago, United States
39% AI deal score
$3,553
From JAX
Elite
Aug 12
Chicago, United States
39% AI deal score
$3,563
From JAX
Elite
Aug 05
Chicago, United States
39% AI deal score
$3,563