How far do most flights from Chicago go?

Historically, the majority of flights from Chicago are long-haul, accounting for 74% of all routes in the trailing 90 days. Medium-haul flights make up 12% of the total, offering a moderate range of travel options. Short-haul flights represent 14% of the routes, providing connections to nearby destinations.

What are the cheapest international destinations from Chicago by country?

Based on historical data from the trailing 90 days, some of the more affordable international destinations from Chicago include Puebla, Mexico, with a median price of $176. Another option is Saskatoon, Canada, which typically sees median prices around $187. While Manistee, United States, is also listed with a median price of $68, it represents a domestic route.

When are flights from Chicago at their lowest price?

Historically, February has been the cheapest month to fly from Chicago, with an average price of $495. This represents a significant savings of 44% compared to the annual median average price of $882. April is typically the second cheapest month, with an average flight price of $589, offering another opportunity for more economical travel.

Flights

From Chicago

Cheap Flights from Chicago

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Deals from

Chicago

RatePunk searches hundreds of travel sites at once for deals on flights from Chicago

Prices updated 7 days ago

456 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 31, 2026.)

Today’s best flight deals from Chicago

Browse current best options from Chicago.

CHI
Fort Lauderdale
United States • 2026-11-15
85% AI deal score
$88
$29
One-way
CHI
Nashville
United States • 2026-10-18
76% AI deal score
$65
$31
One-way
CHI
Washington, D.C.
United States • 2026-11-12
76% AI deal score
$66
$32
One-way
CHI
Atlanta
United States • 2026-09-05
75% AI deal score
$108
$39
One-way
CHI
Phoenix
United States • 2026-12-09
82% AI deal score
$115
$45
One-way
CHI
Orlando
United States • 2026-11-11
77% AI deal score
$76
$45
One-way
CHI
Minneapolis
United States • 2026-10-22
74% AI deal score
$134
$53
One-way
CHI
Las Vegas
United States • 2026-10-04
83% AI deal score
$94
$53
One-way
CHI
San Juan
United States • 2026-09-06
91% AI deal score
$205
$53
One-way
CHI
Los Angeles
United States • 2026-10-20
84% AI deal score
$105
$56
One-way

Flights from Chicago: Overview

Insights for flights from Chicago

Travelers departing from Chicago can reach a substantial number of destinations, with recent data showing access to 1,133 unique cities. Over the last 90 days, the United States accounted for 51% of recent fares, making it the dominant country for flight deals from Chicago. Mexico and Ireland also represent significant portions, each comprising 5% of recent fares. This broad reach provides extensive options for various travel plans.

For those seeking cheap flights from Chicago, the most economical fares right now include trips to Nashville for $61, Washington, D.C. for $64, and Fort Lauderdale for $66. These prices represent the lowest available roundtrip fares to these destinations, offering budget-friendly options for domestic travel.

The route mix from Chicago over the last 90 days indicates a strong preference for longer journeys, with 74% of routes being long-haul. Short-haul flights make up 14% of the routes, while medium-haul flights account for 12%. This distribution suggests that a significant portion of flights from Chicago are for international or transcontinental travel.

When looking at the most frequently discounted destinations from Chicago, Dublin consistently appears in recent fare data. London and Rome are also among the most popular routes, frequently appearing in recent fare observations over the last 90 days. These destinations represent some of the most sought-after international routes for travelers departing from Chicago.

Regarding direct flights from Chicago, approximately 22.8% of recent fares are non-stop. This indicates that while direct options are available, a majority of recent flight deals from Chicago involve at least one connection, classifying the origin as connecting-dominant for travelers.

Most popular airlines from Chicago

United Airlines

American Airlines

Delta Air Lines

Southwest Airlines

Alaska Airlines, Inc.

Air Canada

JetBlue Airways

Spirit Airlines

Last-minute flights going from Chicago soon

Thu, Sep 10

⌛ Last-Minute

MDW - Kigali

Chicago (MDW) - Kigali (KGL)

KLM

$1,774

$966

One-way

Mon, Sep 7

⌛ Last-Minute

MDW - Phuket City

Chicago (MDW) - Phuket City (HKT)

Deutsche Luft Hansa

$1,711

$1,059

One-way

Mon, Sep 7

⌛ Last-Minute

MDW - Mount Kilimanjaro

Chicago (MDW) - Mount Kilimanjaro (JRO)

Deutsche Luft Hansa

$1,742

$1,183

One-way

Sun, Sep 13

⌛ Last-Minute

MDW - Jeddah

Chicago (MDW) - Jeddah (JED)

KLM

$1,140

$799

One-way

Mon, Sep 7

⌛ Last-Minute

ORD - Ahmedabad

Chicago (ORD) - Ahmedabad (AMD)

Etihad Airways

$1,209

$873

One-way

Wed, Sep 9

⌛ Last-Minute

MDW - Jakarta

Chicago (MDW) - Jakarta (CGK)

Deutsche Luft Hansa

$1,261

$900

One-way

Most popular destinations to fly from Chicago

London

TOP

United Kingdom • Jan 2027

from

$287

Kigali

TOP

Rwanda • Sep 2026

from

$966

Riyadh

TOP

Saudi Arabia • Jan 2027

from

$578

Lisbon

TOP

Portugal • May 2027

from

$630

Copenhagen

TOP

Denmark • Apr 2027

from

$522

Cairo

TOP

Egypt • Sep 2026

from

$637

Biggest price drops on international destinations from Chicago

-40%

MDW - Kigali

$1,607 → $966

-49%

MDW - Riyadh

$1,138 → $578

-32%

MDW - Mount Kilimanjaro

$1,742 → $1,183

-29%

MDW - Entebbe

$1,361 → $961

Popular Airports from Chicago

Chicago airport insights

🗓️ Best days to catch a deal

Thu - Tue - Sat

The best days to find deals from Chicago are Thursday, Tuesday, and Saturday.

💸 Cheapest deals found

From ~$28 direct / ~$61 roundtrip

Cheapest flights from Chicago are to destinations within the United States, including Nashville and Fort Lauderdale.

✈️ Airlines to watch

Allegiant Air, Frontier Airlines, Southwest Airlines, Viva Aerobus

Low-cost and regional carriers offer a variety of domestic and international routes from Chicago.

⏱️ Best time to book

2-8 weeks in advance

Booking 2-8 weeks in advance tends to offer the best prices for flights from Chicago.

📅 Cheapest travel period

Apr, Sep - Oct

Flights from Chicago tend to be cheaper in April, September, and October.

🎯 Booking tip

Compare nearby airports first

Flights from RFD start at $32, while flights from ORD start at $2.

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 ~$52

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 ~$58

Chicago Rockford International (RFD)

Rockford International serves travelers in the wider region looking for alternative flight options.

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

💸 Flights from ~$60

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers a major international alternative with significant carrier presence and direct flight options.

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

💸 Flights from ~$101

Business & First Class Flight Deals from Chicago

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

Elite

British Airways, +1

Business Class

From ORD

Elite

Amsterdam

Netherlands • Dec 2026

95% AI deal score

$19,908

$4,972

Save $14,936

British Airways, +1

Business Class

From ORD

Elite

San Diego

United States • Oct 2026

93% AI deal score

$1,319

$705

Save $614

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Los Angeles

United States • Oct 2026

93% AI deal score

$1,195

$376

Save $819

Frontier Airlines

Business Class

From ORD

Elite

San Diego

United States • Nov 2026

93% AI deal score

$1,126

$687

Save $439

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Milan

Italy • Apr 2027

92% AI deal score

$3,102

$1,263

Save $1,839

Scandinavian Airlines

Business Class

From ORD

Elite

Helsinki

Finland • Oct 2026

91% AI deal score

$2,125

$1,098

Save $1,027

Scandinavian Airlines

Business Class

From ORD

Elite

Athens

Greece • Apr 2027

91% AI deal score

$2,916

$1,170

Save $1,746

Scandinavian Airlines

Business Class

From ORD

Elite

Zürich

Switzerland • Oct 2026

91% AI deal score

$2,678

$1,176

Save $1,502

Scandinavian Airlines

Business Class

From ORD

Elite

Copenhagen

Denmark • May 2027

91% AI deal score

$1,874

$1,210

Save $664

Scandinavian Airlines

Business Class

Booking Flights from Chicago: Frequently Asked Questions

Historically, several destinations from Chicago have offered median prices under $150. For example, flights to Manistee typically cost around $68, while Kirksville averages about $79. Other options include Decatur at a median of $93 and Marion at $94. Owensboro also frequently sees prices around $100, based on data from the trailing 90 days.

In the trailing 90 days, flights from Chicago have historically reached 150 unique countries. Travelers can find deals to 1133 distinct cities across these countries. The United States accounts for a significant portion of these destinations, representing 51% of the available deals. Mexico and Ireland are also popular, each making up 5% of the country distribution.

Across the trailing quarter, some of the most frequently served flight destinations from Chicago include Dublin, Ireland. London, United Kingdom, is another consistently popular choice for travelers. Rome, Italy, also stands out as one of the top destinations, indicating a strong historical demand for these international routes.

Explore More Destinations from Chicago

Search more flights

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Departing from nearby city?

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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.

Air Canada

JetBlue Airways

Spirit Airlines

Last-minute flights going from Chicago soon

Thu, Sep 10

⌛ Last-Minute

MDW - Kigali

Chicago (MDW) - Kigali (KGL)

KLM

$1,774

$966

One-way

Mon, Sep 7

⌛ Last-Minute

MDW - Phuket City

Chicago (MDW) - Phuket City (HKT)

Deutsche Luft Hansa

$1,711

$1,059

One-way

Mon, Sep 7

⌛ Last-Minute

MDW - Mount Kilimanjaro

Chicago (MDW) - Mount Kilimanjaro (JRO)

Deutsche Luft Hansa

$1,742

$1,183

One-way

Sun, Sep 13

⌛ Last-Minute

MDW - Jeddah

Chicago (MDW) - Jeddah (JED)

KLM

$1,140

$799

One-way

Mon, Sep 7

⌛ Last-Minute

ORD - Ahmedabad

Chicago (ORD) - Ahmedabad (AMD)

Etihad Airways

$1,209

$873

One-way

Wed, Sep 9

⌛ Last-Minute

MDW - Jakarta

Chicago (MDW) - Jakarta (CGK)

Deutsche Luft Hansa

$1,261

$900

One-way

Most popular destinations to fly from Chicago

London

TOP

United Kingdom • Jan 2027

from

$287

Kigali

TOP

Rwanda • Sep 2026

from

$966

Riyadh

TOP

Saudi Arabia • Jan 2027

from

$578

Lisbon

TOP

Portugal • May 2027

from

$630

Copenhagen

TOP

Denmark • Apr 2027

from

$522

Cairo

TOP

Egypt • Sep 2026

from

$637

Biggest price drops on international destinations from Chicago

-40%

MDW - Kigali

$1,607 → $966

-49%

MDW - Riyadh

$1,138 → $578

-32%

MDW - Mount Kilimanjaro

$1,742 → $1,183

-29%

MDW - Entebbe

$1,361 → $961

Popular Airports from Chicago

Chicago airport insights

🗓️ Best days to catch a deal

Thu - Tue - Sat

The best days to find deals from Chicago are Thursday, Tuesday, and Saturday.

💸 Cheapest deals found

From ~$28 direct / ~$61 roundtrip

Cheapest flights from Chicago are to destinations within the United States, including Nashville and Fort Lauderdale.

✈️ Airlines to watch

Allegiant Air, Frontier Airlines, Southwest Airlines, Viva Aerobus

Low-cost and regional carriers offer a variety of domestic and international routes from Chicago.

⏱️ Best time to book

2-8 weeks in advance

Booking 2-8 weeks in advance tends to offer the best prices for flights from Chicago.

📅 Cheapest travel period

Apr, Sep - Oct

Flights from Chicago tend to be cheaper in April, September, and October.

🎯 Booking tip

Compare nearby airports first

Flights from RFD start at $32, while flights from ORD start at $2.

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 ~$52

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 ~$58

Chicago Rockford International (RFD)

Rockford International serves travelers in the wider region looking for alternative flight options.

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

💸 Flights from ~$60

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers a major international alternative with significant carrier presence and direct flight options.

Denmark • May 2027

91% AI deal score

$1,874

$1,210

Save $664

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

Thu - Tue - Sat

From ~$28 direct / ~$61 roundtrip

Allegiant Air, Frontier Airlines, Southwest Airlines, Viva Aerobus

2-8 weeks in advance

Apr, Sep - Oct

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

Mendoza

Paris

Amsterdam

San Diego

Los Angeles

San Diego

Milan

Helsinki

Athens

Zürich

Copenhagen

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

Thu - Tue - Sat

From ~$28 direct / ~$61 roundtrip

Allegiant Air, Frontier Airlines, Southwest Airlines, Viva Aerobus

2-8 weeks in advance

Apr, Sep - Oct

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

Mendoza

Paris

Amsterdam

San Diego

Los Angeles

San Diego

Milan

Helsinki

Athens

Zürich

Copenhagen

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