Cheap Flights from Chicago to Orlando
Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Chicago
RatePunk searches hundreds of travel sites at once for deals on flights to Orlando
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 Orlando
Explore current cheapest deals departing from Chicago to Orlando
Round trip
Sort by: Cheapest
August 10 - August 24
RFD - Orlando
$120
$77
Round trip
October 14 - October 30
RFD - Orlando
$163
$89
Round trip
August 21 - August 24
RFD - Orlando
$141
$90
Round trip
October 14 - October 28
RFD - Orlando
$166
$90
Round trip
August 17 - August 24
RFD - Orlando
$136
$92
Round trip
August 3 - August 24
RFD - Orlando
$113
$97
Round trip
September 8 - September 15
ORD - Orlando
$143
$98
Round trip
October 19 - October 26
ORD - Orlando
$185
$98
Round trip
September 21 - October 5
ORD - Orlando
$137
$98
Round trip
August 14 - August 24
RFD - Orlando
$127
$99
Round trip
Unlock all 500+ flight deals to Orlando and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Chicago to Orlando
How much is a round trip from Chicago to Orlando
Regular price: $96 - $236
Prices are currently below the regular range.
The regular price range for flights from Chicago to Orlando is between $96 and $236. The current lowest deal is $77 with Allegiant Air, for travel from Aug 10 to Aug 24.
now $77
Low $96
High $236
The cheapest time to fly from Chicago to Orlando
The cheapest month to fly from Chicago to Orlando is September, with a median price of $104. The most expensive month is December, with a median price of $1939. Prices are generally lower from January to October.
September
Flights from $104
December
Flights from $1,939
Direct flights from Chicago to Orlando
Allegiant Air
Frontier Airlines
Last-minute flights going from Chicago to Orlando
Fri, Jul 3
RFD - Orlando
Chicago (RFD) - Orlando (SFB)
Allegiant Air
$136
$105
One-way
Fri, Jul 3
RFD - Orlando
Chicago (RFD) - Orlando (SFB)
Allegiant Air
$271
$173
One-way
Thu, Jul 9
MDW - Orlando
Chicago (MDW) - Orlando (MCO)
Frontier Airlines
$413
$197
One-way
Thu, Jul 9
MDW - Orlando
Chicago (MDW) - Orlando (MCO)
Frontier Airlines
$416
$197
One-way
Thu, Jul 9
MDW - Orlando
Chicago (MDW) - Orlando (MCO)
Frontier Airlines
$485
$230
One-way
Thu, Jul 9
MDW - Orlando
Chicago (MDW) - Orlando (MCO)
Frontier Airlines
$481
$236
One-way
Biggest price drops on these dates for flights from Chicago to Orlando
Dec 22 - Dec 26
$694 → $318
54%
Dec 23 - Dec 30
$684 → $317
54%
Dec 6 - Dec 12
$661 → $296
55%
Dec 23 - Dec 27
$694 → $337
51%
Popular Airports to fly from Chicago to Orlando
Chicago - Orlando route insights
💸 Price insights
Recent fares are above the typical level
Recent fares for Chicago to Orlando are above the typical level, with a median price of $259.
📅 Best time to fly
Fly in September for the best prices
Historically, September offers the lowest median price at $104, making it the cheapest month to fly.
⏱️ Flight duration
Flights typically take 7h 25m
The median flight duration from Chicago to Orlando is 7 hours and 25 minutes.
✈️ Airlines & availability
Frequent deals are available
Deals for flights from Chicago to Orlando are frequent, with over 1 deal per day.
🏆 Airline highlight
Allegiant Air offers direct flights
Allegiant Air is one of the airlines providing direct flight options on this route.
🎯 Booking tip
Consider booking in advance for better prices
Booking in advance can help secure better prices for your trip to Orlando.
Chicago main airports to depart from
Chicago Rockford International (RFD)
Consider Chicago Rockford International for potentially cheaper flights from Chicago to Orlando.
📍 ~120 km from Chicago (reachable by car)
💸 Flights from ~$77
Chicago Midway International (MDW)
Chicago Midway International offers another departure option for your trip to Orlando.
📍 ~15 km from Chicago (reachable by car or public transport)
💸 Flights from ~$175
O Hare International (ORD)
O Hare International is a major airport for flights from Chicago to Orlando.
📍 ~30 km from Chicago (reachable by car or public transport)
💸 Flights from ~$98
Orlando main airports to arrive at
Orlando Sanford International (SFB)
Orlando Sanford International Airport is a good option for budget-conscious travelers flying to Orlando.
📍 ~30 km from Orlando (reachable by car)
💸 Flights from ~$77
Orlando International (MCO)
Orlando International Airport is a convenient choice for travelers visiting Orlando and surrounding areas.
📍 ~15 km from Orlando (reachable by car)
💸 Flights from ~$98
Airports nearby Orlando used as alternative
Tampa International (TPA)
Tampa International is a major international hub with extensive routes, making it a premier alternative for Orlando.
📍 ~135 km from Orlando (reachable by car, but expect heavy traffic).
💸 Flights from ~$97
Daytona Beach International (DAB)
Daytona Beach International is the closest alternative and offers a less crowded terminal experience.
📍 ~80 km from Orlando (reachable by car).
💸 Flights from ~$316
Orlando Melbourne International (MLB)
Orlando Melbourne International is a convenient alternative for travelers on the east side of Orlando.
📍 ~75 km from Orlando (reachable by car).
💸 Flights from ~$292
St. Pete–Clearwater International (PIE)
St. Pete–Clearwater International is a major base for low-cost carriers, providing budget-friendly options.
📍 ~150 km from Orlando (reachable by car).
💸 Flights from ~$92
Sarasota–Bradenton International (SRQ)
Sarasota–Bradenton International is a full-service airport with a growing number of direct domestic connections.
📍 ~180 km from Orlando (reachable by car).
💸 Flights from ~$106
Business & First Class Flight Deals to Orlando
Discover luxury on the budget with premium cabin class on flights from Chicago to Orlando.
Elite
Best Elite deals to Orlando
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From ORD
Elite
Sep 11
Orlando, United States
86% AI deal score
$5,012
$1,894
Save $3,118
From ORD
Elite
Sep 05
Orlando, United States
85% AI deal score
$4,817
$2,073
Save $2,744
From ORD
Elite
Sep 05
Orlando, United States
85% AI deal score
$4,988
$2,128
Save $2,860
From ORD
Elite
Sep 12
Orlando, United States
84% AI deal score
$5,127
$2,097
Save $3,030
From MDW
Elite
Dec 16
Orlando, United States
82% AI deal score
$1,782
$819
Save $963
From MDW
Elite
Aug 20
Orlando, United States
81% AI deal score
$1,454
$739
Save $715
From MDW
Elite
Aug 10
Orlando, United States
81% AI deal score
$1,475
$774
Save $701
From MDW
Elite
Aug 13
Orlando, United States
80% AI deal score
$1,506
$794
Save $712
From MDW
Elite
Jul 15
Orlando, United States
79% AI deal score
$1,081
$707
Save $374
From MDW
Elite
Sep 15
Orlando, United States
77% AI deal score
$1,137
$758
Save $379
From ORD
Elite
Aug 04
Orlando, United States
77% AI deal score
$824
$565
Save $259
From MDW
Elite
Dec 18
Orlando, United States
76% AI deal score
$1,724
$1,062
Save $662
From MDW
Elite
Jun 30
Orlando, United States
75% AI deal score
$1,114
$838
Save $276
From MDW
Elite
Jul 27
Orlando, United States
74% AI deal score
$1,296
$959
Save $337
From MDW
Elite
Nov 16
Orlando, United States
74% AI deal score
$1,325
$959
Save $366
From MDW
Elite
Jun 22
Orlando, United States
74% AI deal score
$1,590
$1,124
Save $466
From MDW
Elite
Oct 15
Orlando, United States
73% AI deal score
$1,276
$943
Save $333
From ORD
Elite
Oct 12
Orlando, United States
72% AI deal score
$3,237
$2,208
Save $1,029
From ORD
Elite
Dec 08
Orlando, United States
72% AI deal score
$966
$757
Save $209
From ORD
Elite
Jul 29
Orlando, United States
71% AI deal score
$2,543
$1,763
Save $780
From ORD
Elite
Jul 05
Orlando, United States
71% AI deal score
$2,502
$1,792
Save $710
From ORD
Elite
Jul 30
Orlando, United States
71% AI deal score
$2,577
$1,795
Save $782
From ORD
Elite
Jul 07
Orlando, United States
71% AI deal score
$641
$565
Save $76
From ORD
Elite
Sep 08
Orlando, United States
71% AI deal score
$729
$565
Save $164
From ORD
Elite
Oct 29
Orlando, United States
71% AI deal score
$736
$581
Save $155
From ORD
Elite
Jul 27
Orlando, United States
70% AI deal score
$2,459
$1,763
Save $696
From ORD
Elite
Jul 11
Orlando, United States
70% AI deal score
$2,286
$1,768
Save $518
From ORD
Elite
Jul 22
Orlando, United States
70% AI deal score
$2,363
$1,768
Save $595
From ORD
Elite
Jul 18
Orlando, United States
70% AI deal score
$2,348
$1,768
Save $580
From ORD
Elite
Jul 24
Orlando, United States
70% AI deal score
$2,375
$1,795
Save $580
From ORD
Elite
Aug 11
Orlando, United States
70% AI deal score
$2,400
$1,795
Save $605
From ORD
Elite
Jul 28
Orlando, United States
70% AI deal score
$2,488
$1,861
Save $627
From ORD
Elite
Jul 06
Orlando, United States
70% AI deal score
$2,556
$1,863
Save $693
From ORD
Elite
Jun 28
Orlando, United States
70% AI deal score
$2,503
$1,863
Save $640
From ORD
Elite
Jul 14
Orlando, United States
70% AI deal score
$637
$565
Save $72
From ORD
Elite
Jul 29
Orlando, United States
70% AI deal score
$637
$565
Save $72
From ORD
Elite
Jul 05
Orlando, United States
69% AI deal score
$2,279
$1,790
Save $489
From ORD
Elite
Jul 27
Orlando, United States
69% AI deal score
$2,363
$1,828
Save $535
From ORD
Elite
Jul 27
Orlando, United States
69% AI deal score
$2,279
$1,828
Save $451
From ORD
Elite
Jul 11
Orlando, United States
69% AI deal score
$2,286
$1,833
Save $453
From ORD
Elite
Jul 22
Orlando, United States
69% AI deal score
$2,285
$1,833
Save $452
From ORD
Elite
Jul 18
Orlando, United States
69% AI deal score
$2,269
$1,835
Save $434
From ORD
Elite
Aug 08
Orlando, United States
69% AI deal score
$2,274
$1,856
Save $418
From ORD
Elite
Jul 23
Orlando, United States
69% AI deal score
$2,367
$1,861
Save $506
From ORD
Elite
Jul 15
Orlando, United States
69% AI deal score
$2,279
$1,861
Save $418
From ORD
Elite
Jul 16
Orlando, United States
69% AI deal score
$2,281
$1,861
Save $420
From ORD
Elite
Jul 06
Orlando, United States
69% AI deal score
$2,277
$1,861
Save $416
From ORD
Elite
Jul 24
Orlando, United States
69% AI deal score
$2,353
$1,863
Save $490
From ORD
Elite
Jul 30
Orlando, United States
69% AI deal score
$2,370
$1,863
Save $507
From ORD
Elite
Jun 29
Orlando, United States
69% AI deal score
$2,468
$1,913
Save $555
From ORD
Elite
Jul 23
Orlando, United States
69% AI deal score
$2,348
$1,927
Save $421
From ORD
Elite
Jul 28
Orlando, United States
69% AI deal score
$2,367
$1,929
Save $438
From ORD
Elite
Aug 12
Orlando, United States
69% AI deal score
$841
$757
Save $84
From MDW
Elite
Aug 09
Orlando, United States
69% AI deal score
$1,200
$966
Save $234
From MDW
Elite
Nov 15
Orlando, United States
69% AI deal score
$1,325
$989
Save $336
From ORD
Elite
Aug 07
Orlando, United States
68% AI deal score
$2,230
$1,927
Save $303
From ORD
Elite
Jul 15
Orlando, United States
68% AI deal score
$2,263
$1,929
Save $334
From ORD
Elite
Jul 16
Orlando, United States
68% AI deal score
$2,263
$1,929
Save $334
From ORD
Elite
Jul 25
Orlando, United States
68% AI deal score
$2,375
$1,992
Save $383
From ORD
Elite
Jul 25
Orlando, United States
68% AI deal score
$2,371
$2,070
Save $301
From ORD
Elite
Jul 08
Orlando, United States
68% AI deal score
$803
$757
Save $46
From ORD
Elite
Oct 13
Orlando, United States
68% AI deal score
$821
$757
Save $64
From ORD
Elite
Jul 07
Orlando, United States
68% AI deal score
$803
$757
Save $46
From MDW
Elite
Jul 01
Orlando, United States
68% AI deal score
$1,143
$964
Save $179
From ORD
Elite
Aug 06
Orlando, United States
67% AI deal score
$2,274
$2,071
Save $203
From ORD
Elite
Jul 25
Orlando, United States
67% AI deal score
$2,269
$2,249
Save $20
From ORD
Elite
Jul 25
Orlando, United States
67% AI deal score
$2,394
$2,260
Save $134
From ORD
Elite
Jul 14
Orlando, United States
67% AI deal score
$775
$757
Save $18
From ORD
Elite
Jul 21
Orlando, United States
67% AI deal score
$781
$757
Save $24
From ORD
Elite
Sep 01
Orlando, United States
67% AI deal score
$775
$757
Save $18
From ORD
Elite
Sep 08
Orlando, United States
67% AI deal score
$778
$757
Save $21
From MDW
Elite
Jul 03
Orlando, United States
67% AI deal score
$1,124
$980
Save $144
From ORD
Elite
Aug 10
Orlando, United States
66% AI deal score
$2,189
$2,168
Save $21
From ORD
Elite
Jul 29
Orlando, United States
66% AI deal score
$2,279
$2,197
Save $82
From ORD
Elite
Jul 22
Orlando, United States
66% AI deal score
$763
$757
Save $6
From ORD
Elite
Jul 29
Orlando, United States
66% AI deal score
$760
$757
Save $3
From MDW
Elite
Aug 06
Orlando, United States
66% AI deal score
$1,541
$1,327
Save $214
From ORD
Elite
Dec 04
Orlando, United States
66% AI deal score
$717
From ORD
Elite
Nov 05
Orlando, United States
66% AI deal score
$741
From ORD
Elite
Nov 28
Orlando, United States
66% AI deal score
$741
From ORD
Elite
Oct 25
Orlando, United States
66% AI deal score
$776
From ORD
Elite
Nov 24
Orlando, United States
66% AI deal score
$795
From MDW
Elite
Aug 16
Orlando, United States
65% AI deal score
$1,465
$1,292
Save $173
From MDW
Elite
Jun 18
Orlando, United States
65% AI deal score
$1,687
$1,503
Save $184
From ORD
Elite
Oct 30
Orlando, United States
49% AI deal score
$968
From ORD
Elite
Nov 12
Orlando, United States
49% AI deal score
$1,022
From MDW
Elite
Aug 04
Orlando, United States
49% AI deal score
$1,411
$1,307
Save $104
From MDW
Elite
Oct 24
Orlando, United States
49% AI deal score
$1,415
$1,327
Save $88
From ORD
Elite
Oct 28
Orlando, United States
48% AI deal score
$1,077
From ORD
Elite
Nov 15
Orlando, United States
48% AI deal score
$1,077
From MDW
Elite
Nov 21
Orlando, United States
48% AI deal score
$1,163
$1,114
Save $49
From MDW
Elite
Dec 10
Orlando, United States
48% AI deal score
$1,354
$1,307
Save $47
From MDW
Elite
Sep 14
Orlando, United States
47% AI deal score
$1,308
$1,307
Save $1
From MDW
Elite
Oct 09
Orlando, United States
47% AI deal score
$1,336
$1,327
Save $9
From MDW
Elite
Dec 17
Orlando, United States
47% AI deal score
$1,510
$1,492
Save $18
From ORD
Elite
Jun 20
Orlando, United States
46% AI deal score
$2,912
From ORD
Elite
Jun 20
Orlando, United States
45% AI deal score
$2,920
From MDW
Elite
Aug 11
Orlando, United States
44% AI deal score
$1,256
From ORD
Elite
Nov 26
Orlando, United States
44% AI deal score
$1,289
From ORD
Elite
Jun 20
Orlando, United States
43% AI deal score
$3,511