FlightsFrom Orlando

To Chicago

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

September 14 - September 28

Cheapest

SFB - Chicago

$106

$90

Round trip

September 11 - September 28

Cheapest

SFB - Chicago

$103

$90

Round trip

September 25 - September 28

Cheapest
Best

SFB - Chicago

$125

$90

Round trip

October 2 - October 14

Cheapest

SFB - Chicago

$109

$90

Round trip

October 5 - October 14

Cheapest

SFB - Chicago

$118

$90

Round trip

August 24 - August 31

Earliest

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

Right now, 15% of recent fares for flights from Orlando to Chicago are classified as a good price. Over the last 90 days, fares for this route typically range from $94 to $216, with a median of $120. Currently, prices are above the typical level, so you may want to monitor fares for potential drops. New deals appear almost daily, offering frequent opportunities to find better prices.
If you are looking for cheap flights from Orlando to Chicago, the cheapest months to fly are typically September, with a median fare of $99, followed by October at $101, and August at $106. Planning your trip during these months can help you secure more budget-friendly options.
A typical journey from Orlando to Chicago takes about 5h 56m, including connections. This is a medium-haul route, covering a distance of 1595 km. Given that a meaningful share of itineraries are non-stop, the rest connect once, so you can expect a balance of direct and connecting flight options.
When flying from Orlando to Chicago, 52.8% of recent fares are for direct flights from Orlando to Chicago. For itineraries that include connections, the median number of stopovers is 1. This indicates a mixed offering of both non-stop and connecting flights, giving you flexibility in choosing your preferred travel style.

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

Cheapest

Flights from $99

January

Most Expensive

Flights from $382

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

Direct flights from Orlando to Chicago

Airline logo

Allegiant Air

Airline logo

Frontier Airlines

Airline logo

Southwest Airlines

Last-minute flights going from Orlando to Chicago

Sun, Jun 21

⌛ Last-Minute

SFB - Chicago

Allegiant Air

Orlando (SFB) - Chicago (MDW)

Allegiant Air

$332

$255

One-way

Sat, Jun 27

⌛ Last-Minute

SFB - Chicago

Allegiant Air

Orlando (SFB) - Chicago (RFD)

Allegiant Air

$329

$248

One-way

Sun, Jul 5

⌛ Last-Minute

SFB - Chicago

Allegiant Air

Orlando (SFB) - Chicago (MDW)

Allegiant Air

$270

$204

One-way

Mon, Jul 6

⌛ Last-Minute

MCO - Chicago

Frontier Airlines

Orlando (MCO) - Chicago (MDW)

Frontier Airlines

$269

$196

One-way

Tue, Jul 7

⌛ Last-Minute

MCO - Chicago

Frontier Airlines

Orlando (MCO) - Chicago (MDW)

Frontier Airlines

$270

$183

One-way

Wed, Jul 8

⌛ Last-Minute

SFB - Chicago

Allegiant Air

Orlando (SFB) - Chicago (RFD)

Allegiant Air

$129

$100

One-way

Biggest price drops on these dates for flights from Orlando to Chicago

5 nights

Aug 12 - Aug 17

$261  →  $150

43%

5 nights

Aug 16 - Aug 21

$291  →  $184

37%

2 nights

Aug 15 - Aug 17

$267  →  $164

39%

4 nights

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)

Cheapest

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)

Cheapest

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)

Cheapest

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

Frequently Asked Questions About Flights to Chicago

Historically, the best prices for flights from Orlando to Chicago are found when booking 60+ days in advance. Across the trailing quarter, the average price for flights booked in this window was $132. Prices tend to increase as the departure date approaches, with flights booked 0-6 days out averaging $497. Booking 28-59 days in advance typically yields an average price of $177, while booking 14-27 days out averages $188.

Based on historical data from the trailing 90 days, a good price for a flight from Orlando to Chicago is typically $94 or less. The median price for this route has been $120. Prices can go up, with 75% of observed prices being $216 or less. This threshold of $94 represents a competitive price point for travelers.

Historically, the cheapest months to fly from Orlando to Chicago are September, October, and August. In September, the median price was $99, and in October, it was $101. August also offered competitive prices with a median of $106. The annual median price for this route is $120, indicating these months are typically more affordable.