Cheap Flights from Orlando to Chicago
Browse current best options from Orlando. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Orlando
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 Orlando to Chicago
Explore current cheapest deals departing from Orlando to Chicago
Round trip
Sort by: Cheapest
September 14 - September 28
SFB - Chicago
$106
$90
Round trip
September 11 - September 28
SFB - Chicago
$103
$90
Round trip
September 25 - September 28
SFB - Chicago
$125
$90
Round trip
October 2 - October 14
SFB - Chicago
$109
$90
Round trip
October 5 - October 14
SFB - Chicago
$118
$90
Round trip
August 24 - August 31
SFB - Chicago
$114
$92
Round trip
October 7 - October 14
SFB - Chicago
$124
$96
Round trip
September 21 - October 19
MCO - Chicago
$105
$98
Round trip
October 26 - November 16
MCO - Chicago
$122
$98
Round trip
September 14 - September 21
MCO - Chicago
$118
$98
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 Orlando to Chicago
How much is a round trip from Orlando to Chicago
Regular price: $88 - $183
Prices for flights from Orlando to Chicago are currently within the regular range.
The regular price range for this route is $88 to $183. The current lowest deal is $90 with Allegiant Air, for travel from September 14 to September 28.
now $90
Low $88
High $183
The cheapest time to fly from Orlando to Chicago
The cheapest month to fly from Orlando to Chicago is September, with a median price of $99. The most expensive month is January, with a median price of $382. Prices are generally lower from April to November.
September
Flights from $99
January
Flights from $382
Direct flights from Orlando to Chicago
Allegiant Air
Frontier Airlines
Southwest Airlines
Last-minute flights going from Orlando to Chicago
Sun, Jun 21
SFB - Chicago
Orlando (SFB) - Chicago (MDW)
Allegiant Air
$332
$255
One-way
Sat, Jun 27
SFB - Chicago
Orlando (SFB) - Chicago (RFD)
Allegiant Air
$329
$248
One-way
Sun, Jul 5
SFB - Chicago
Orlando (SFB) - Chicago (MDW)
Allegiant Air
$270
$204
One-way
Mon, Jul 6
MCO - Chicago
Orlando (MCO) - Chicago (MDW)
Frontier Airlines
$269
$196
One-way
Tue, Jul 7
MCO - Chicago
Orlando (MCO) - Chicago (MDW)
Frontier Airlines
$270
$183
One-way
Wed, Jul 8
SFB - Chicago
Orlando (SFB) - Chicago (RFD)
Allegiant Air
$129
$100
One-way
Biggest price drops on these dates for flights from Orlando to Chicago
Aug 12 - Aug 17
$261 → $150
43%
Aug 16 - Aug 21
$291 → $184
37%
Aug 15 - Aug 17
$267 → $164
39%
Oct 27 - Oct 31
$272 → $169
38%
Popular Airports to fly from Orlando to Chicago
Orlando - Chicago route insights
💸 Price insights
Recent fares are above the typical level
Recent fares from Orlando to Chicago are above the typical level of $120.
📅 Best time to fly
Fly in September for deals around $99
Historically, September is the cheapest month to fly, with a median price of $99.
⏱️ Flight duration
Expect flights to take 5h 56m
The typical flight duration from Orlando to Chicago is 5 hours and 56 minutes.
✈️ Airlines & availability
Frequent deals are available
Deals on flights from Orlando to Chicago are frequent, with over 1 deal per day.
🏆 Airline highlight
Allegiant Air offers deals from $90
Allegiant Air recently offered a deal for $90 from Orlando Sanford International to Chicago Rockford International.
🎯 Booking tip
Good prices are available 15% of the time
Historically, 15% of recent fares from Orlando to Chicago were considered a good price.
Orlando main airports to depart from
Orlando Sanford International (SFB)
Orlando Sanford International Airport offers a budget-friendly option for flights from Orlando to Chicago.
📍 ~20 km from Orlando (reachable by car).
💸 Flights from ~$90
Orlando International (MCO)
Orlando International Airport is a convenient choice for flights from Orlando to Chicago.
📍 ~15 km from Orlando (reachable by car).
💸 Flights from ~$98
Chicago main airports to arrive at
Chicago Rockford International (RFD)
Fly into Chicago Rockford International for a budget-friendly option when traveling to Chicago.
📍 ~120 km from Chicago (reachable by car)
💸 Flights from ~$90
Chicago Midway International (MDW)
Choose Chicago Midway International for a convenient arrival point closer to downtown Chicago.
📍 ~15 km from Chicago (reachable by car)
💸 Flights from ~$186
O Hare International (ORD)
Arrive at O Hare International, a major hub offering many connections to Chicago and beyond.
📍 ~25 km from Chicago (reachable by car)
💸 Flights from ~$98
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
This airport offers excellent proximity to Chicago with high-frequency flight options and direct rail access.
📍 ~135 km from Chicago (reachable by car or train)
💸 Flights from ~$177
South Bend International (SBN)
This airport is geographically the closest alternative to the Chicago area with direct commuter rail access.
📍 ~125 km from Chicago (reachable by car or train)
💸 Flights from ~$83
Gerald R. Ford International (GRR)
This major regional hub is a good alternative for travelers on the eastern side of the Chicago metro area.
📍 ~235 km from Chicago (reachable by car)
💸 Flights from ~$84
Dane County Regional (MSN)
This reliable regional airport offers consistent service and is less congested than major Chicago airports.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$139
Fort Wayne International (FWA)
This airport provides stable regional service and is an alternative for travelers in the southeastern Chicago suburbs.
📍 ~250 km from Chicago (reachable by car)
💸 Flights from ~$125
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Orlando to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From MCO
Elite
Jul 15
Chicago, United States
80% AI deal score
$836
$565
Save $271
From MCO
Elite
Jul 22
Chicago, United States
80% AI deal score
$836
$565
Save $271
From MCO
Elite
Jul 14
Chicago, United States
80% AI deal score
$836
$565
Save $271
From MCO
Elite
Sep 24
Chicago, United States
77% AI deal score
$1,330
$774
Save $556
From MCO
Elite
Aug 26
Chicago, United States
77% AI deal score
$863
$565
Save $298
From MCO
Elite
Jul 15
Chicago, United States
75% AI deal score
$1,007
$728
Save $279
From MCO
Elite
Sep 03
Chicago, United States
75% AI deal score
$1,175
$773
Save $402
From MCO
Elite
Sep 03
Chicago, United States
75% AI deal score
$1,175
$773
Save $402
From MCO
Elite
Sep 03
Chicago, United States
75% AI deal score
$1,210
$774
Save $436
From MCO
Elite
Sep 13
Chicago, United States
75% AI deal score
$1,295
$834
Save $461
From MCO
Elite
Jul 23
Chicago, United States
75% AI deal score
$1,595
$1,021
Save $574
From MCO
Elite
Aug 31
Chicago, United States
74% AI deal score
$1,024
$723
Save $301
From MCO
Elite
Oct 14
Chicago, United States
74% AI deal score
$1,059
$768
Save $291
From MCO
Elite
Sep 03
Chicago, United States
74% AI deal score
$1,190
$789
Save $401
From MCO
Elite
Sep 03
Chicago, United States
74% AI deal score
$1,179
$789
Save $390
From MCO
Elite
Sep 02
Chicago, United States
73% AI deal score
$963
$723
Save $240
From MCO
Elite
Sep 03
Chicago, United States
73% AI deal score
$1,189
$824
Save $365
From MCO
Elite
Sep 03
Chicago, United States
73% AI deal score
$1,179
$834
Save $345
From MCO
Elite
Aug 29
Chicago, United States
72% AI deal score
$1,023
$773
Save $250
From MCO
Elite
Aug 29
Chicago, United States
72% AI deal score
$1,023
$773
Save $250
From MCO
Elite
Aug 31
Chicago, United States
72% AI deal score
$1,020
$773
Save $247
From MCO
Elite
Oct 21
Chicago, United States
71% AI deal score
$788
$565
Save $223
From MCO
Elite
Sep 01
Chicago, United States
68% AI deal score
$967
$757
Save $210
From MCO
Elite
Sep 02
Chicago, United States
68% AI deal score
$968
$757
Save $211
From MCO
Elite
Sep 02
Chicago, United States
68% AI deal score
$967
$757
Save $210
From MCO
Elite
Aug 26
Chicago, United States
68% AI deal score
$839
$757
Save $82
From MCO
Elite
Aug 18
Chicago, United States
68% AI deal score
$833
$757
Save $76
From MCO
Elite
Aug 12
Chicago, United States
68% AI deal score
$844
$757
Save $87
From MCO
Elite
Aug 11
Chicago, United States
68% AI deal score
$845
$757
Save $88
From MCO
Elite
Aug 29
Chicago, United States
68% AI deal score
$1,023
$789
Save $234
From MCO
Elite
Aug 29
Chicago, United States
68% AI deal score
$1,023
$789
Save $234
From MCO
Elite
Aug 31
Chicago, United States
68% AI deal score
$1,020
$789
Save $231
From MCO
Elite
Aug 31
Chicago, United States
68% AI deal score
$1,020
$789
Save $231
From MCO
Elite
Oct 16
Chicago, United States
68% AI deal score
$1,085
$818
Save $267
From MCO
Elite
Sep 03
Chicago, United States
68% AI deal score
$1,175
$889
Save $286
From MCO
Elite
Jul 09
Chicago, United States
68% AI deal score
$1,310
$997
Save $313
From MCO
Elite
Aug 08
Chicago, United States
68% AI deal score
$1,798
$1,272
Save $526
From MCO
Elite
Oct 25
Chicago, United States
68% AI deal score
$795
$696
Save $99
From MCO
Elite
Jul 15
Chicago, United States
67% AI deal score
$806
$757
Save $49
From MCO
Elite
Oct 06
Chicago, United States
67% AI deal score
$820
$757
Save $63
From MCO
Elite
Sep 01
Chicago, United States
67% AI deal score
$960
$773
Save $187
From MCO
Elite
Sep 01
Chicago, United States
67% AI deal score
$960
$773
Save $187
From MCO
Elite
Sep 02
Chicago, United States
67% AI deal score
$960
$773
Save $187
From MCO
Elite
Aug 30
Chicago, United States
67% AI deal score
$1,023
$808
Save $215
From MCO
Elite
Aug 30
Chicago, United States
67% AI deal score
$1,023
$808
Save $215
From MCO
Elite
Aug 29
Chicago, United States
67% AI deal score
$1,023
$824
Save $199
From MCO
Elite
Aug 30
Chicago, United States
67% AI deal score
$1,023
$824
Save $199
From MCO
Elite
Aug 30
Chicago, United States
67% AI deal score
$1,023
$824
Save $199
From MCO
Elite
Aug 31
Chicago, United States
67% AI deal score
$1,020
$824
Save $196
From MCO
Elite
Aug 29
Chicago, United States
67% AI deal score
$1,027
$834
Save $193
From MCO
Elite
Aug 31
Chicago, United States
67% AI deal score
$1,025
$834
Save $191
From MCO
Elite
Jul 09
Chicago, United States
67% AI deal score
$1,339
$1,059
Save $280
From MCO
Elite
Aug 07
Chicago, United States
67% AI deal score
$1,865
$1,327
Save $538
From MCO
Elite
Aug 14
Chicago, United States
67% AI deal score
$1,833
$1,327
Save $506
From MCO
Elite
Oct 16
Chicago, United States
67% AI deal score
$793
$616
Save $177
From MCO
Elite
Sep 13
Chicago, United States
67% AI deal score
$840
$632
Save $208
From MCO
Elite
Jul 31
Chicago, United States
66% AI deal score
$1,851
$1,729
Save $122
From MCO
Elite
Jul 31
Chicago, United States
66% AI deal score
$1,857
$1,729
Save $128
From MCO
Elite
Jul 08
Chicago, United States
66% AI deal score
$1,985
$1,769
Save $216
From MCO
Elite
Jul 08
Chicago, United States
66% AI deal score
$1,886
$1,769
Save $117
From MCO
Elite
Sep 01
Chicago, United States
66% AI deal score
$960
$808
Save $152
From MCO
Elite
Sep 02
Chicago, United States
66% AI deal score
$960
$808
Save $152
From MCO
Elite
Sep 04
Chicago, United States
66% AI deal score
$971
$808
Save $163
From MCO
Elite
Sep 04
Chicago, United States
66% AI deal score
$971
$808
Save $163
From MCO
Elite
Sep 01
Chicago, United States
66% AI deal score
$968
$818
Save $150
From MCO
Elite
Sep 02
Chicago, United States
66% AI deal score
$968
$818
Save $150
From MCO
Elite
Sep 04
Chicago, United States
66% AI deal score
$971
$824
Save $147
From MCO
Elite
Sep 04
Chicago, United States
66% AI deal score
$966
$824
Save $142
From MCO
Elite
Aug 30
Chicago, United States
66% AI deal score
$1,023
$859
Save $164
From MCO
Elite
Aug 30
Chicago, United States
66% AI deal score
$1,027
$869
Save $158
From MCO
Elite
Jul 30
Chicago, United States
66% AI deal score
$1,243
$1,021
Save $222
From MCO
Elite
Jul 08
Chicago, United States
65% AI deal score
$1,826
$1,764
Save $62
From MCO
Elite
Jul 08
Chicago, United States
65% AI deal score
$1,828
$1,769
Save $59
From MCO
Elite
Jul 31
Chicago, United States
65% AI deal score
$1,855
$1,790
Save $65
From MCO
Elite
Jul 31
Chicago, United States
65% AI deal score
$1,867
$1,790
Save $77
From MCO
Elite
Jul 31
Chicago, United States
65% AI deal score
$1,863
$1,790
Save $73
From MCO
Elite
Aug 05
Chicago, United States
65% AI deal score
$1,927
$1,856
Save $71
From MCO
Elite
Jul 31
Chicago, United States
65% AI deal score
$1,938
$1,863
Save $75
From MCO
Elite
Jul 08
Chicago, United States
65% AI deal score
$2,027
$1,911
Save $116
From MCO
Elite
Aug 29
Chicago, United States
65% AI deal score
$1,023
$889
Save $134
From MCO
Elite
Aug 31
Chicago, United States
65% AI deal score
$1,024
$889
Save $135
From MCO
Elite
Oct 09
Chicago, United States
65% AI deal score
$1,445
$1,193
Save $252
From MCO
Elite
Jul 08
Chicago, United States
50% AI deal score
$1,813
$1,764
Save $49
From MCO
Elite
Aug 05
Chicago, United States
50% AI deal score
$1,825
$1,795
Save $30
From MCO
Elite
Aug 05
Chicago, United States
50% AI deal score
$1,829
$1,795
Save $34
From MCO
Elite
Jul 08
Chicago, United States
50% AI deal score
$1,824
$1,797
Save $27
From MCO
Elite
Jul 08
Chicago, United States
50% AI deal score
$1,826
$1,797
Save $29
From MCO
Elite
Jul 08
Chicago, United States
50% AI deal score
$1,896
$1,863
Save $33
From MCO
Elite
Jul 08
Chicago, United States
50% AI deal score
$1,890
$1,863
Save $27
From MCO
Elite
Jul 08
Chicago, United States
50% AI deal score
$1,887
$1,863
Save $24
From MCO
Elite
Jul 08
Chicago, United States
50% AI deal score
$1,895
$1,863
Save $32
From MCO
Elite
Aug 05
Chicago, United States
50% AI deal score
$1,970
$1,927
Save $43
From MCO
Elite
Sep 01
Chicago, United States
50% AI deal score
$757
From MCO
Elite
Sep 09
Chicago, United States
50% AI deal score
$757
From MCO
Elite
Sep 04
Chicago, United States
50% AI deal score
$969
$859
Save $110
From MCO
Elite
Sep 04
Chicago, United States
50% AI deal score
$981
$869
Save $112
From MCO
Elite
Aug 05
Chicago, United States
49% AI deal score
$1,856
From MCO
Elite
Jul 31
Chicago, United States
49% AI deal score
$1,873
$1,861
Save $12
From MCO
Elite
Sep 01
Chicago, United States
49% AI deal score
$757
From MCO
Elite
Sep 01
Chicago, United States
49% AI deal score
$968
$873
Save $95