Cheap Flights from Tampa to Chicago
Browse current best options from Tampa. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Tampa
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
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 Tampa to Chicago
Explore current cheapest deals departing from Tampa to Chicago
Round trip
Sort by: Cheapest
October 2 - October 5
PIE - Chicago
$124
$84
Round trip
August 14 - August 31
PIE - Chicago
$101
$100
Round trip
November 13 - November 16
PIE - Chicago
$141
$100
Round trip
November 6 - November 16
PIE - Chicago
$129
$100
Round trip
September 18 - October 5
PIE - Chicago
$105
$105
Round trip
August 7 - August 31
PIE - Chicago
$96
$107
Round trip
September 18 - September 21
PIE - Chicago
$121
$108
Round trip
October 2 - October 14
PIE - Chicago
$110
$109
Round trip
October 2 - October 19
PIE - Chicago
$107
$109
Round trip
August 28 - August 31
PIE - Chicago
$118
$110
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 Tampa to Chicago
How much is a round trip from Tampa to Chicago
Regular price: $103 - $231
Prices are currently below the regular range for flights from Tampa to Chicago.
The regular price range for flights from Tampa to Chicago is $103 to $231. The current lowest deal is $84 with Allegiant Air, for travel from Oct 2-Oct 5.
now $84
Low $103
High $231
The cheapest time to fly from Tampa to Chicago
The cheapest month to fly from Tampa to Chicago is September, with a median price of $125. The most expensive month is December, with a median price of $613. Prices are generally lower from April to November.
September
Flights from $125
December
Flights from $613
Direct flights from Tampa to Chicago
Allegiant Air
Last-minute flights going from Tampa to Chicago
Fri, Jun 19
TPA - Chicago
Tampa (TPA) - Chicago (MDW)
Frontier Airlines
$419
$320
One-way
Sat, Jun 20
TPA - Chicago
Tampa (TPA) - Chicago (MDW)
Frontier Airlines
$413
$279
One-way
Sun, Jun 21
PIE - Chicago
Tampa (PIE) - Chicago (MDW)
Allegiant Air
$352
$283
One-way
Fri, Jun 26
PIE - Chicago
Tampa (PIE) - Chicago (RFD)
Allegiant Air
$316
$261
One-way
Tue, Jul 7
TPA - Chicago
Tampa (TPA) - Chicago (MDW)
Frontier Airlines
$289
$227
One-way
Wed, Jul 8
TPA - Chicago
Tampa (TPA) - Chicago (RFD)
JetBlue Airways
$293
$201
One-way
Biggest price drops on these dates for flights from Tampa to Chicago
Jun 20 - Jun 23
$413 → $279
32%
Oct 2 - Oct 6
$264 → $159
40%
Sep 16 - Sep 21
$269 → $164
39%
Jun 19 - Jun 20
$419 → $320
24%
Popular Airports to fly from Tampa to Chicago
Tampa - Chicago route insights
💸 Price insights
Recent fares are above the typical level
Recent fares from TPA to CHI are above the typical level, with 21% of deals considered good.
📅 Best time to fly
September is historically the cheapest month to fly
Historically, September is the cheapest month to fly from Tampa to Chicago, with a median price of $125.
⏱️ Flight duration
Flights from Tampa to Chicago take 7h 15m
The median flight duration from Tampa to Chicago is 7 hours 15 minutes, including layovers.
✈️ Airlines & availability
Connecting flights are more common for this route
Connecting flights make up 61.3% of deals, with a median of 1 stopover when connecting.
🏆 Airline highlight
Allegiant Air offers direct flights
Allegiant Air has offered direct flights from Tampa to Chicago in recent deals.
🎯 Booking tip
Deals appear frequently for this route
Deals for flights from Tampa to Chicago appear frequently, averaging 1.03 deals per day.
Tampa main airports to depart from
St. Pete–Clearwater International (PIE)
St. Pete–Clearwater International offers flights to Chicago, potentially at a lower price.
📍 ~25 km from Tampa (reachable by car)
💸 Flights from ~$84
Tampa International (TPA)
Tampa International is a convenient option for flights to Chicago.
📍 ~8 km from Tampa (reachable by car)
💸 Flights from ~$105
Chicago main airports to arrive at
Chicago Rockford International (RFD)
Consider Chicago Rockford International for flights from Tampa to Chicago, with prices starting from $84.
📍 ~120 km from Chicago (reachable by car)
💸 Flights from ~$84
Chicago Midway International (MDW)
Consider Chicago Midway International for flights from Tampa to Chicago, with prices starting from $185.
📍 ~15 km from Chicago (reachable by car)
💸 Flights from ~$185
O Hare International (ORD)
Consider O Hare International for flights from Tampa to Chicago, with prices starting from $185.
📍 ~25 km from Chicago (reachable by car)
💸 Flights from ~$185
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.
📍 ~100 km from Chicago (reachable by rail)
💸 Flights from ~$266
South Bend International (SBN)
South Bend International is the geographically closest alternative to Chicago, with direct commuter rail connections.
📍 ~120 km from Chicago (reachable by rail)
💸 Flights from ~$96
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub, offering a wide range of cabin classes.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$104
Dane County Regional (MSN)
Dane County Regional is a reliable regional airport with consistent service and a full range of cabin classes.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$139
Fort Wayne International (FWA)
Fort Wayne International offers stable regional service and can be an alternative for southeastern Chicago suburbs.
📍 ~230 km from Chicago (reachable by car)
💸 Flights from ~$129
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Tampa to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From TPA
Elite
Jun 16
Chicago, United States
82% AI deal score
$2,146
$1,039
Save $1,107
From TPA
Elite
Jun 16
Chicago, United States
81% AI deal score
$2,327
$777
Save $1,550
From TPA
Elite
Oct 10
Chicago, United States
80% AI deal score
$1,565
$819
Save $746
From TPA
Elite
Oct 27
Chicago, United States
78% AI deal score
$1,467
$874
Save $593
From TPA
Elite
Jun 17
Chicago, United States
77% AI deal score
$1,593
$975
Save $618
From TPA
Elite
Sep 02
Chicago, United States
75% AI deal score
$1,224
$831
Save $393
From TPA
Elite
Jul 09
Chicago, United States
75% AI deal score
$1,408
$946
Save $462
From TPA
Elite
Jun 16
Chicago, United States
74% AI deal score
$1,002
$761
Save $241
From TPA
Elite
Oct 08
Chicago, United States
73% AI deal score
$1,356
$994
Save $362
From TPA
Elite
Oct 08
Chicago, United States
73% AI deal score
$1,564
$1,109
Save $455
From TPA
Elite
Aug 12
Chicago, United States
68% AI deal score
$986
$891
Save $95
From TPA
Elite
Sep 17
Chicago, United States
67% AI deal score
$1,209
$986
Save $223
From TPA
Elite
Oct 28
Chicago, United States
67% AI deal score
$774
$711
Save $63
From TPA
Elite
Aug 26
Chicago, United States
67% AI deal score
$796
$711
Save $85
From TPA
Elite
Aug 22
Chicago, United States
67% AI deal score
$801
$711
Save $90
From TPA
Elite
Aug 01
Chicago, United States
67% AI deal score
$791
$711
Save $80
From TPA
Elite
Aug 05
Chicago, United States
66% AI deal score
$2,159
$1,949
Save $210
From TPA
Elite
Aug 05
Chicago, United States
66% AI deal score
$2,066
$1,949
Save $117
From TPA
Elite
Aug 07
Chicago, United States
66% AI deal score
$2,159
$1,972
Save $187
From TPA
Elite
Oct 26
Chicago, United States
66% AI deal score
$2,100
$2,049
Save $51
From TPA
Elite
Oct 08
Chicago, United States
66% AI deal score
$2,198
$2,113
Save $85
From TPA
Elite
Aug 10
Chicago, United States
66% AI deal score
$2,215
$2,162
Save $53
From TPA
Elite
Jul 25
Chicago, United States
66% AI deal score
$904
$879
Save $25
From TPA
Elite
Jul 21
Chicago, United States
66% AI deal score
$907
$879
Save $28
From TPA
Elite
Aug 04
Chicago, United States
66% AI deal score
$912
$879
Save $33
From TPA
Elite
Aug 05
Chicago, United States
66% AI deal score
$907
$879
Save $28
From TPA
Elite
Aug 28
Chicago, United States
66% AI deal score
$933
$891
Save $42
From TPA
Elite
Jul 24
Chicago, United States
66% AI deal score
$914
$891
Save $23
From TPA
Elite
Jul 26
Chicago, United States
66% AI deal score
$915
$891
Save $24
From TPA
Elite
Jul 23
Chicago, United States
66% AI deal score
$915
$891
Save $24
From TPA
Elite
Oct 23
Chicago, United States
66% AI deal score
$929
$903
Save $26
From TPA
Elite
Sep 22
Chicago, United States
66% AI deal score
$748
$711
Save $37
From TPA
Elite
Sep 02
Chicago, United States
66% AI deal score
$752
$711
Save $41
From TPA
Elite
Oct 28
Chicago, United States
66% AI deal score
$752
$723
Save $29
From TPA
Elite
Jul 08
Chicago, United States
65% AI deal score
$2,054
$1,974
Save $80
From TPA
Elite
Sep 27
Chicago, United States
65% AI deal score
$2,120
$2,119
Save $1
From TPA
Elite
Nov 07
Chicago, United States
65% AI deal score
$891
$879
Save $12
From TPA
Elite
Aug 26
Chicago, United States
65% AI deal score
$887
$879
Save $8
From TPA
Elite
Aug 12
Chicago, United States
65% AI deal score
$894
$879
Save $15
From TPA
Elite
Jul 25
Chicago, United States
65% AI deal score
$888
$879
Save $9
From TPA
Elite
Jul 26
Chicago, United States
65% AI deal score
$904
$892
Save $12
From TPA
Elite
Jul 08
Chicago, United States
50% AI deal score
$1,999
$1,974
Save $25
From TPA
Elite
Aug 02
Chicago, United States
50% AI deal score
$2,054
$2,011
Save $43
From TPA
Elite
Jul 31
Chicago, United States
50% AI deal score
$2,048
$2,011
Save $37
From TPA
Elite
Jul 24
Chicago, United States
50% AI deal score
$891
From TPA
Elite
Jul 22
Chicago, United States
50% AI deal score
$709
From TPA
Elite
Nov 07
Chicago, United States
50% AI deal score
$711
From TPA
Elite
Sep 02
Chicago, United States
50% AI deal score
$713
$711
Save $2
From TPA
Elite
Jul 21
Chicago, United States
50% AI deal score
$711
From TPA
Elite
Jul 25
Chicago, United States
50% AI deal score
$711
From TPA
Elite
Jul 15
Chicago, United States
50% AI deal score
$711
From TPA
Elite
Jul 22
Chicago, United States
50% AI deal score
$711
From TPA
Elite
Jul 14
Chicago, United States
50% AI deal score
$711
From TPA
Elite
Jul 15
Chicago, United States
50% AI deal score
$711
From TPA
Elite
Jul 25
Chicago, United States
50% AI deal score
$711
From TPA
Elite
Jul 21
Chicago, United States
50% AI deal score
$711
From TPA
Elite
Jul 18
Chicago, United States
50% AI deal score
$711
From TPA
Elite
Nov 21
Chicago, United States
50% AI deal score
$723
From TPA
Elite
Nov 07
Chicago, United States
50% AI deal score
$723
From TPA
Elite
Oct 08
Chicago, United States
49% AI deal score
$2,113
From TPA
Elite
Oct 31
Chicago, United States
49% AI deal score
$879
From TPA
Elite
Oct 24
Chicago, United States
49% AI deal score
$879
From TPA
Elite
Aug 29
Chicago, United States
49% AI deal score
$879
From TPA
Elite
Oct 17
Chicago, United States
49% AI deal score
$879
From TPA
Elite
Jul 16
Chicago, United States
49% AI deal score
$1,609
$1,467
Save $142
From TPA
Elite
Oct 03
Chicago, United States
48% AI deal score
$879
From TPA
Elite
Jul 22
Chicago, United States
48% AI deal score
$879
From TPA
Elite
Jul 25
Chicago, United States
48% AI deal score
$879
From TPA
Elite
Jul 18
Chicago, United States
48% AI deal score
$880
From TPA
Elite
Jul 24
Chicago, United States
48% AI deal score
$891
From TPA
Elite
Sep 24
Chicago, United States
48% AI deal score
$1,436
$1,344
Save $92
From TPA
Elite
Sep 27
Chicago, United States
47% AI deal score
$2,119
From TPA
Elite
Sep 26
Chicago, United States
47% AI deal score
$879
From TPA
Elite
Sep 29
Chicago, United States
47% AI deal score
$880
From TPA
Elite
Oct 19
Chicago, United States
47% AI deal score
$903
From TPA
Elite
Nov 03
Chicago, United States
47% AI deal score
$922
From TPA
Elite
Aug 03
Chicago, United States
47% AI deal score
$776
$723
Save $53
From TPA
Elite
Aug 05
Chicago, United States
46% AI deal score
$2,112
From TPA
Elite
Jun 25
Chicago, United States
46% AI deal score
$1,047
$1,025
Save $22
From TPA
Elite
Oct 08
Chicago, United States
46% AI deal score
$743
$723
Save $20
From TPA
Elite
Jul 08
Chicago, United States
45% AI deal score
$2,068
From TPA
Elite
Oct 26
Chicago, United States
45% AI deal score
$2,138
From TPA
Elite
Aug 05
Chicago, United States
44% AI deal score
$2,112
From TPA
Elite
Aug 10
Chicago, United States
44% AI deal score
$2,162
From TPA
Elite
Aug 04
Chicago, United States
44% AI deal score
$2,162
From TPA
Elite
Aug 04
Chicago, United States
44% AI deal score
$2,162
From TPA
Elite
Jun 30
Chicago, United States
43% AI deal score
$2,158
From TPA
Elite
Jun 30
Chicago, United States
43% AI deal score
$2,162
From TPA
Elite
Nov 06
Chicago, United States
43% AI deal score
$1,073
From TPA
Elite
Dec 05
Chicago, United States
42% AI deal score
$1,073
From TPA
Elite
Nov 01
Chicago, United States
42% AI deal score
$1,073
From TPA
Elite
Nov 05
Chicago, United States
42% AI deal score
$1,073
From TPA
Elite
Oct 29
Chicago, United States
42% AI deal score
$1,073
From TPA
Elite
Sep 10
Chicago, United States
40% AI deal score
$1,344
From TPA
Elite
Jun 18
Chicago, United States
39% AI deal score
$3,588
From TPA
Elite
Jul 10
Chicago, United States
39% AI deal score
$3,745
From TPA
Elite
Oct 09
Chicago, United States
39% AI deal score
$988
From TPA
Elite
Jul 02
Chicago, United States
39% AI deal score
$1,469
From TPA
Elite
Jul 13
Chicago, United States
38% AI deal score
$3,301
From TPA
Elite
Jul 18
Chicago, United States
37% AI deal score
$1,687