How far do most flights from Chicago go?

Across the trailing 90 days, the majority of flights from Chicago are long-haul, accounting for 74% of all routes. Medium-haul flights represent 12% of the total. Short-haul destinations make up 14% of the flights from Chicago.

What are the cheapest international destinations from Chicago by country?

Historically, some of the more affordable international destinations from Chicago include Puebla, Mexico, with a median price of $176. Flights to Saskatoon, Canada, typically average around $187. For domestic travel, Manistee in the United States has a median price of $68.

When are flights from Chicago at their lowest price?

Flights from Chicago are historically at their lowest price in February, with an average price of $495. This represents a significant saving of 44% compared to the annual median average price of $882. April is also a more affordable month for travel, with an average price of $589.

Flights

From Chicago

Cheap Flights from Chicago

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 from Chicago

Prices updated today

454 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Aug 25, 2026.)

Today’s best flight deals from Chicago

Browse current best options from Chicago.

CHI
Fort Lauderdale
United States • 2026-11-12
86% AI deal score
$91
$28
One-way
CHI
Nashville
United States • 2026-09-06
74% AI deal score
$77
$30
One-way
CHI
Washington, D.C.
United States • 2026-09-26
78% AI deal score
$76
$32
One-way
CHI
Phoenix
United States • 2026-12-09
83% AI deal score
$117
$45
One-way
CHI
Orlando
United States • 2026-11-09
74% AI deal score
$76
$50
One-way
CHI
San Juan
United States • 2026-08-31
91% AI deal score
$203
$52
One-way
CHI
Minneapolis
United States • 2026-10-06
73% AI deal score
$132
$53
One-way
CHI
Las Vegas
United States • 2026-09-13
83% AI deal score
$94
$53
One-way
CHI
Tampa
United States • 2026-10-30
75% AI deal score
$88
$54
One-way
CHI
Los Angeles
United States • 2026-10-09
85% AI deal score
$105
$54
One-way

Flights from Chicago: Overview

Insights for flights from Chicago

Travelers from Chicago can reach a substantial number of destinations, with recent fares showing availability to 1,133 unique cities. Over the last 90 days, the United States accounts for 51% of recent fares from Chicago, making it the most frequent destination country. Other notable countries include Mexico, at 5%, and Ireland, also at 5% of recent fares. This broad distribution provides numerous options for finding cheap flights from Chicago.

Right now, the cheapest fares from Chicago start at $50 to Atlanta. You can also find economical options to Nashville for $61 and Washington, D.C. for $65. These prices represent the lowest available roundtrip fares, offering good value for domestic travel.

The route mix from Chicago heavily favors longer-distance journeys, with 74% of routes classified as long-haul. Short-haul flights make up 14% of the routes, while medium-haul flights account for 12%. This indicates that a significant majority of flights from Chicago are for international or cross-country trips.

When looking for flight deals from Chicago, you'll find that Dublin is the most frequently discounted destination in recent months. London and Rome also appear often among recent fares, indicating these European capitals are popular and well-served routes from Chicago. This suggests consistent opportunities for deals to these cities over the last 90 days.

Only 22.8% of recent fares from Chicago are direct flights, indicating that connecting flights are the more common option for travelers. This means that while direct flights from Chicago are available, you are more likely to find routes that include at least one stop to your final destination.

Most popular airlines from Chicago

United Airlines

American Airlines

Delta Air Lines

Southwest Airlines

Alaska Airlines, Inc.

JetBlue Airways

Air Canada

WestJet

Last-minute flights going from Chicago soon

Tue, Aug 25

⌛ Last-Minute

MDW - Johannesburg

Chicago (MDW) - Johannesburg (JNB)

Virgin Atlantic

$2,046

$1,027

One-way

Sun, Aug 30

⌛ Last-Minute

MDW - Nagasaki

Chicago (MDW) - Nagasaki (NGS)

Deutsche Luft Hansa

$1,927

$1,125

One-way

Sat, Aug 29

⌛ Last-Minute

MDW - Anchorage

Chicago (MDW) - Anchorage (ANC)

Deutsche Luft Hansa

$846

$539

One-way

Wed, Sep 2

⌛ Last-Minute

ORD - Bangkok

Chicago (ORD) - Bangkok (BKK)

Etihad Airways

$1,086

$773

One-way

Sun, Aug 30

⌛ Last-Minute

ORD - Kochi

Chicago (ORD) - Kochi (COK)

Etihad Airways

$1,243

$846

One-way

Thu, Aug 27

⌛ Last-Minute

MDW - Gothenburg

Chicago (MDW) - Gothenburg (GOT)

Deutsche Luft Hansa

$1,398

$848

One-way

Most popular destinations to fly from Chicago

Cape Town

TOP

South Africa • Aug 2026

from

$977

Copenhagen

TOP

Denmark • Apr 2027

from

$497

Riyadh

TOP

Saudi Arabia • Jan 2027

from

$578

Mumbai

TOP

India • Aug 2026

from

$681

Hong Kong

TOP

Hong Kong • Sep 2026

from

$686

Cairo

TOP

Egypt • Oct 2026

from

$716

Biggest price drops on international destinations from Chicago

-36%

MDW - Addis Ababa

$2,220 → $1,415

-33%

MDW - Angeles

$1,913 → $1,277

-43%

ORD - Hong Kong

$1,258 → $716

-32%

MDW - Davao

$1,633 → $1,106

Popular Airports from Chicago

Chicago airport insights

🗓️ Best days to catch a deal

Tue - Sat

Flights from Chicago are cheapest on Tuesday and Saturday, with deals as low as $23.

💸 Cheapest deals found

From ~$30 direct / ~$50 roundtrip

The most affordable flights from Chicago are to destinations within the United States, such as Atlanta and Nashville.

✈️ Airlines to watch

Allegiant Air, Frontier Airlines, Southwest Airlines, Porter Airlines

Low-cost and regional carriers consistently offer the cheapest fares from Chicago.

⏱️ Best time to book

2-8 weeks in advance

Booking 2-8 weeks in advance from Chicago is optimal, with prices tending to rise closer to departure.

📅 Cheapest travel period

Apr, Aug, Jan

Flights from Chicago tend to be lower priced in April, August, and January.

🎯 Booking tip

Compare nearby airports first

Rockford (RFD) offers a median fare of $420, which is $509 cheaper than Chicago O'Hare (ORD).

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International is ideal for travelers seeking a wide range of domestic and international flight options.

📍 ~25 km from Chicago city center (reachable by car or train)

💸 Flights from ~$50

Chicago Midway International (MDW)

Midway International is suitable for travelers looking for convenient access to downtown Chicago and regional flights.

📍 ~14 km from Chicago city center (reachable by car or train)

💸 Flights from ~$96

Chicago Rockford International (RFD)

Rockford International is a good option for travelers in the western Chicago suburbs or northern Illinois.

📍 ~126 km from Chicago city center (reachable by car)

💸 Flights from ~$61

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options, easily accessible from Chicago.

📍 ~121 km from Chicago (reachable by car or train)

💸 Flights from ~$142

Business & First Class Flight Deals from Chicago

Discover luxury on the budget with premium cabin class on flights from Chicago.

Elite

Best Elite deals from Chicago

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From ORD

Elite

Cairo

Egypt • Nov 2026

95% AI deal score

$12,307

$4,711

Save $7,596

British Airways, +1

Business Class

From ORD

Elite

Amsterdam

Netherlands • Nov 2026

95% AI deal score

$13,372

$4,973

Save $8,399

British Airways

Business Class

From ORD

Elite

Bergen

Norway • Apr 2027

94% AI deal score

$3,019

$926

Save $2,093

Scandinavian Airlines

Business Class

From ORD

Elite

Trondheim

Norway • Apr 2027

93% AI deal score

$2,734

$969

Save $1,765

Scandinavian Airlines

Business Class

From ORD

Elite

Milan

Italy • Apr 2027

93% AI deal score

$3,104

$1,162

Save $1,942

Scandinavian Airlines

Business Class

From ORD

Elite

San Diego

United States • Oct 2026

93% AI deal score

$1,274

$727

Save $547

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Mexico City

Mexico • Nov 2026

93% AI deal score

$1,005

$587

Save $418

Aeroméxico

Business Class

From ORD

Elite

Los Angeles

United States • Oct 2026

93% AI deal score

$1,209

$356

Save $853

Frontier Airlines

Business Class

From ORD

Elite

Indianapolis

United States • Sep 2026

93% AI deal score

$593

$357

Save $236

United Airlines

Business Class

From ORD

Elite

Stuttgart

Germany • Apr 2027

92% AI deal score

$2,968

$1,164

Save $1,804

Scandinavian Airlines

Business Class

From ORD

Elite

Copenhagen

Denmark • Apr 2027

92% AI deal score

$1,863

$1,164

Save $699

Scandinavian Airlines

Business Class

From ORD

Elite

Amsterdam

Netherlands • Apr 2027

92% AI deal score

$2,844

$1,166

Save $1,678

Scandinavian Airlines

Business Class

Booking Flights from Chicago: Frequently Asked Questions

Historically, several destinations from Chicago have had median prices under $150. For example, flights to Manistee typically cost around $68, while Kirksville averages about $79. Other affordable options in the trailing 90 days include Decatur at $93 and Marion at $94. Owensboro also presents a good value with a median price of $100.

From Chicago, travelers can typically reach 150 unique countries, with flights available to 1133 different cities. Across the trailing quarter, the United States accounted for 51% of the available destinations. Mexico and Ireland were also popular, each representing 5% of the available routes.

Historically, some of the most frequently served flight destinations from Chicago include Dublin, Ireland. London, United Kingdom, is another prominent destination for travelers departing from Chicago. Rome, Italy, also stands out as one of the top locations for flights in the trailing 90 days.

Explore More Destinations from Chicago

Search more flights

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Departing from nearby city?

Flights from Fort Wayne Flights from Grand Rapids Flights from Madison Flights from Milwaukee Flights from South Bend

Flights from Chicago: Overview

Insights for flights from Chicago

Most popular airlines from Chicago

United Airlines

American Airlines

Delta Air Lines

Southwest Airlines

Alaska Airlines, Inc.

JetBlue Airways

Air Canada

WestJet

Last-minute flights going from Chicago soon

Tue, Aug 25

⌛ Last-Minute

MDW - Johannesburg

Chicago (MDW) - Johannesburg (JNB)

Virgin Atlantic

$2,046

$1,027

One-way

Sun, Aug 30

⌛ Last-Minute

MDW - Nagasaki

Chicago (MDW) - Nagasaki (NGS)

Deutsche Luft Hansa

$1,927

$1,125

One-way

Sat, Aug 29

⌛ Last-Minute

MDW - Anchorage

Chicago (MDW) - Anchorage (ANC)

Deutsche Luft Hansa

$846

$539

One-way

Wed, Sep 2

⌛ Last-Minute

ORD - Bangkok

Chicago (ORD) - Bangkok (BKK)

Etihad Airways

$1,086

$773

One-way

Sun, Aug 30

⌛ Last-Minute

ORD - Kochi

Chicago (ORD) - Kochi (COK)

Etihad Airways

$1,243

$846

One-way

Thu, Aug 27

⌛ Last-Minute

MDW - Gothenburg

Chicago (MDW) - Gothenburg (GOT)

Deutsche Luft Hansa

$1,398

$848

One-way

Most popular destinations to fly from Chicago

Cape Town

TOP

South Africa • Aug 2026

from

$977

Copenhagen

TOP

Denmark • Apr 2027

from

$497

Riyadh

TOP

Saudi Arabia • Jan 2027

from

$578

Mumbai

TOP

India • Aug 2026

from

$681

Hong Kong

TOP

Hong Kong • Sep 2026

from

$686

Cairo

TOP

Egypt • Oct 2026

from

$716

Biggest price drops on international destinations from Chicago

-36%

MDW - Addis Ababa

$2,220 → $1,415

-33%

MDW - Angeles

$1,913 → $1,277

-43%

ORD - Hong Kong

$1,258 → $716

-32%

MDW - Davao

$1,633 → $1,106

Popular Airports from Chicago

Chicago airport insights

🗓️ Best days to catch a deal

Tue - Sat

Flights from Chicago are cheapest on Tuesday and Saturday, with deals as low as $23.

💸 Cheapest deals found

From ~$30 direct / ~$50 roundtrip

The most affordable flights from Chicago are to destinations within the United States, such as Atlanta and Nashville.

✈️ Airlines to watch

Allegiant Air, Frontier Airlines, Southwest Airlines, Porter Airlines

Low-cost and regional carriers consistently offer the cheapest fares from Chicago.

⏱️ Best time to book

2-8 weeks in advance

Booking 2-8 weeks in advance from Chicago is optimal, with prices tending to rise closer to departure.

📅 Cheapest travel period

Apr, Aug, Jan

Flights from Chicago tend to be lower priced in April, August, and January.

🎯 Booking tip

Compare nearby airports first

Rockford (RFD) offers a median fare of $420, which is $509 cheaper than Chicago O'Hare (ORD).

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International is ideal for travelers seeking a wide range of domestic and international flight options.

📍 ~25 km from Chicago city center (reachable by car or train)

💸 Flights from ~$50

Chicago Midway International (MDW)

Midway International is suitable for travelers looking for convenient access to downtown Chicago and regional flights.

📍 ~14 km from Chicago city center (reachable by car or train)

💸 Flights from ~$96

Chicago Rockford International (RFD)

Rockford International is a good option for travelers in the western Chicago suburbs or northern Illinois.

📍 ~126 km from Chicago city center (reachable by car)

💸 Flights from ~$61

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options, easily accessible from Chicago.

Netherlands • Apr 2027

92% AI deal score

$2,844

$1,166

Save $1,678

Scandinavian Airlines

Business Class

Booking Flights from Chicago: Frequently Asked Questions

Cheap Flights from Chicago

Today’s best flight deals from Chicago

Flights from Chicago: Overview

Insights for flights from Chicago

Most popular airlines from Chicago

Last-minute flights going from Chicago soon

Most popular destinations to fly from Chicago

Biggest price drops on international destinations from Chicago

Popular Airports from Chicago

Chicago airport insights

Tue - Sat

From ~$30 direct / ~$50 roundtrip

Allegiant Air, Frontier Airlines, Southwest Airlines, Porter Airlines

2-8 weeks in advance

Apr, Aug, Jan

Compare nearby airports first

Chicago main airports to depart from

Airports nearby Chicago used as alternative

Business & First Class Flight Deals from Chicago

Best Elite deals from Chicago

Cairo

Amsterdam

Bergen

Trondheim

Milan

San Diego

Mexico City

Los Angeles

Indianapolis

Stuttgart

Copenhagen

Amsterdam

Booking Flights from Chicago: Frequently Asked Questions

Which destinations from Chicago are under 150 USD?

How many countries can I reach from Chicago?

What are the top flight destinations from Chicago?

How far do most flights from Chicago go?

What are the cheapest international destinations from Chicago by country?

When are flights from Chicago at their lowest price?

Explore More Destinations from Chicago

Search more flights

Departing from nearby city?

Flights from Chicago: Overview

Insights for flights from Chicago

Most popular airlines from Chicago

Last-minute flights going from Chicago soon

Most popular destinations to fly from Chicago

Biggest price drops on international destinations from Chicago

Popular Airports from Chicago

Chicago airport insights

Tue - Sat

From ~$30 direct / ~$50 roundtrip

Allegiant Air, Frontier Airlines, Southwest Airlines, Porter Airlines

2-8 weeks in advance

Apr, Aug, Jan

Compare nearby airports first

Chicago main airports to depart from

Airports nearby Chicago used as alternative

Business & First Class Flight Deals from Chicago

Best Elite deals from Chicago

Cairo

Amsterdam

Bergen

Trondheim

Milan

San Diego

Mexico City

Los Angeles

Indianapolis

Stuttgart

Copenhagen

Amsterdam

Booking Flights from Chicago: Frequently Asked Questions

Which destinations from Chicago are under 150 USD?

How many countries can I reach from Chicago?

What are the top flight destinations from Chicago?

How far do most flights from Chicago go?

What are the cheapest international destinations from Chicago by country?

When are flights from Chicago at their lowest price?

Explore More Destinations from Chicago