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 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.)

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Today’s best flight deals from Chicago

Explore current cheapest deals departing from Chicago

One-way

Sort by: Cheapest

RFD

Nashville

United States • Aug 2026

$71

$30

One-way

ORD

Denver

United States • Oct 2026

$91

$33

One-way

RFD

Fort Lauderdale

United States • Aug 2026

$92

$34

One-way

ORD

Houston

United States • Oct 2026

$95

$35

One-way

RFD

Tampa

United States • Aug 2026

$91

$38

One-way

RFD

Orlando

United States • Oct 2026

$116

$38

One-way

MDW

Destin

United States • Aug 2026

$90

$40

One-way

ORD

Dallas

United States • Aug 2026

$80

$42

One-way

ORD

Atlanta

United States • Sep 2026

$74

$45

One-way

RFD

Phoenix

United States • Aug 2026

$108

$45

One-way

Unlock all 500+ flight deals from Chicago and get alerts when great deals appear

Origin Intelligence — 2,412 Destinations from Chicago Tracked

Insights for flights from Chicago

Travelers from Chicago can reach a substantial number of destinations, with 2,412 unique cities available over the last 90 days. The United States accounts for the largest share of recent fares at 37%, followed by Ireland at 9%, and the United Kingdom at 6%. This indicates a strong focus on domestic travel, alongside significant international routes to European countries.

For those seeking cheap flights from Chicago, right now the most economical destinations include Nashville, with fares starting at $64. You can also find flights to Fort Lauderdale from $67, and to Denver from $75. These prices represent some of the lowest available for travelers departing from Chicago.

The majority of flights from Chicago involve connections, as only 22.8% of recent fares were for non-stop routes. This suggests that while direct flights from Chicago are available, travelers should expect to consider itineraries with layovers for a broader range of options or potentially lower prices.

Looking at the most popular routes, Dublin in Ireland stands out as the most frequently discounted destination from Chicago. Following Dublin, London in the United Kingdom and Rome in Italy are also among the destinations that appear most often in recent fare observations. These cities consistently offer a higher volume of available deals for travelers.

The flight distances from Chicago are predominantly long-haul, with 74% of routes categorized as long-distance international trips. Short-haul flights make up 14% of the routes, while medium-haul flights account for 12%. This distribution highlights Chicago's role as a major hub for extended international travel.

Most popular airlines from Chicago

United Airlines

American Airlines

Southwest Airlines

Deutsche Luft Hansa

Alaska Airlines, Inc.

Air Canada

Spirit Airlines

JetBlue Airways

Last-minute flights going from Chicago soon

Sat, Jun 27

⌛ Last-Minute

ORD - Bogotá

Chicago (ORD) - Bogotá (BOG)

LATAM Chile

$732

$413

One-way

Thu, Jun 18

⌛ Last-Minute

MDW - Quito

Chicago (MDW) - Quito (UIO)

LATAM Chile

$821

$502

One-way

Wed, Jun 17

⌛ Last-Minute

ORD - Rio de Janeiro

Chicago (ORD) - Rio de Janeiro (GIG)

LATAM Chile

$900

$608

One-way

Wed, Jun 17

⌛ Last-Minute

MDW - Porto Alegre

Chicago (MDW) - Porto Alegre (POA)

LATAM Chile

$1,235

$861

One-way

Tue, Jun 23

⌛ Last-Minute

MDW - Mumbai

Chicago (MDW) - Mumbai (BOM)

Deutsche Luft Hansa

$1,215

$921

One-way

Sat, Jun 27

⌛ Last-Minute

MDW - Brasília

Chicago (MDW) - Brasília (BSB)

LATAM Chile

$1,086

$830

One-way

Most popular destinations to fly from Chicago

Athens

TOP

Greece • Feb 2027

from

$638

Milan

TOP

Italy • Mar 2027

from

$569

Zürich

TOP

Switzerland • Mar 2027

from

$592

Marrakesh

TOP

Morocco • Mar 2027

from

$666

Istanbul

TOP

Turkey • Mar 2027

from

$703

New Delhi

TOP

India • May 2027

from

$712

Biggest price drops on international destinations from Chicago

-59%

ORD - New Delhi

$1,746 → $712

-45%

ORD - Shanghai

$1,537 → $847

-43%

ORD - Athens

$1,116 → $638

-30%

MDW - Kirmington

$1,599 → $1,123

Popular Airports from Chicago

Chicago airport insights

🎯 Booking tip

Compare nearby airports first

Rockford (RFD) offers a median fare of $325, $466 cheaper than Chicago O'Hare (ORD).

📅 Cheapest travel period

Jan

Flights from Chicago tend to be cheaper in January.

⏱️ Best time to book

2-8 weeks in advance

Booking 2-8 weeks in advance offers the best prices from Chicago, with fares tending to rise closer to departure.

✈️ Airlines to watch

United Airlines, American Airlines, Southwest Airlines, Deutsche Luft Hansa

Major US carriers provide extensive domestic and international flight options from Chicago.

💸 Cheapest deals found

From ~$30 direct / ~$64 roundtrip

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

🗓️ Best days to catch a deal

Tue - Sat - Thu

The cheapest flights from Chicago are on Tuesday, Saturday, and Thursday, with fares as low as $22.

Chicago main airports to depart from

Chicago Rockford International (RFD)

Cheapest

Chicago Rockford International is ideal for travelers seeking budget-friendly flights from the wider Chicago area.

📍 ~120 km from Chicago (reachable by car)

💸 Flights from ~$61

Chicago Midway International (MDW)

Chicago Midway International is a convenient option for travelers flying to various domestic destinations.

📍 ~15 km from Chicago (reachable by car or train)

💸 Flights from ~$86

O Hare International (ORD)

O Hare International is suitable for travelers looking for extensive domestic and international flight options.

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

💸 Flights from ~$66

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers excellent proximity to Chicago with high-frequency flight options and diverse cabin class availability.

📍 ~125 km from Chicago (reachable by car or train)

💸 Flights from ~$157

South Bend International (SBN)

South Bend International is a close alternative to Chicago, offering easier security and parking with direct rail connections.

📍 ~135 km from Chicago (reachable by car or train)

💸 Flights from ~$69

Gerald R. Ford International (GRR)

Cheapest

Gerald R. Ford International is a major regional hub with a wide range of cabin classes, ideal for eastern Chicago travelers.

📍 ~220 km from Chicago (reachable by car)

💸 Flights from ~$63

Dane County Regional (MSN)

Dane County Regional is a reliable, less congested regional airport with consistent service and a full range of cabin classes.

📍 ~225 km from Chicago (reachable by car)

💸 Flights from ~$128

Fort Wayne International (FWA)

Fort Wayne International offers stable regional service and multiple cabin class options for travelers in southeastern Chicago suburbs.

📍 ~240 km from Chicago (reachable by car)

💸 Flights from ~$78

Business & First Class Flight Deals from Chicago

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

Elite

Alaska Airlines, Inc., +1

Business Class

From ORD

Elite

St. Louis

United States • Aug 2026

93% AI deal score

$609

$352

Save $257

United Airlines

Business Class

From ORD

Elite

Cleveland

United States • Jul 2026

93% AI deal score

$612

$357

Save $255

United Airlines

Business Class

From ORD

Elite

Madison

United States • Jun 2026

93% AI deal score

$849

$482

Save $367

United Airlines

Business Class

From ORD

Elite

San Diego

United States • Oct 2026

93% AI deal score

$1,139

$717

Save $422

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Cairo

Egypt • Aug 2026

93% AI deal score

$8,459

$4,707

Save $3,752

British Airways

Business Class

From ORD

Elite

Guadalajara

Mexico • Aug 2026

92% AI deal score

$1,013

$546

Save $467

Aeroméxico

Business Class

From ORD

Elite

Mexico City

Mexico • Sep 2026

92% AI deal score

$1,247

$711

Save $536

Aeroméxico

Business Class

From ORD

Elite

Lima

Peru • Jul 2026

92% AI deal score

$3,209

$1,636

Save $1,573

Copa Airlines

Business Class

From ORD

Elite

Honolulu

United States • Mar 2027

92% AI deal score

$3,101

$1,950

Save $1,151

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Kahului

United States • Mar 2027

92% AI deal score

$3,081

$1,972

Save $1,109

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Warsaw

Poland • Aug 2026

91% AI deal score

$2,419

$1,299

Save $1,120

Scandinavian Airlines

Business Class

From ORD

Elite

Montreal

Canada • Oct 2026

91% AI deal score

$829

$538

Save $291

United Airlines

Business Class

From ORD

Elite

Cincinnati

United States • Aug 2026

91% AI deal score

$502

$357

Save $145

United Airlines

Business Class

From ORD

Elite

Columbus

United States • Aug 2026

91% AI deal score

$514

$357

Save $157

United Airlines

Business Class

From ORD

Elite

Minneapolis

United States • Jul 2026

90% AI deal score

$426

$329

Save $97

United Airlines

Business Class

From ORD

Elite

Gdańsk

Poland • Aug 2026

89% AI deal score

$2,298

$1,281

Save $1,017

Scandinavian Airlines

Business Class

From ORD

Elite

Guadalajara

Mexico • Aug 2026

89% AI deal score

$1,066

$718

Save $348

Aeroméxico

Business Class

From ORD

Elite

Stockholm

Sweden • Sep 2026

88% AI deal score

$1,928

$1,220

Save $708

Scandinavian Airlines

Business Class

From ORD

Elite

Kauai

United States • Jan 2027

88% AI deal score

$3,885

$1,919

Save $1,966

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Oslo

Norway • Nov 2026

87% AI deal score

$2,285

$1,226

Save $1,059

Scandinavian Airlines

Business Class

From ORD

Elite

Los Angeles

United States • Aug 2026

87% AI deal score

$826

$472

Save $354

Frontier

Business Class

From ORD

Elite

San Francisco

United States • Sep 2026

87% AI deal score

$951

$562

Save $389

Frontier

Business Class

From ORD

Elite

Milwaukee

United States • Sep 2026

86% AI deal score

$493

$385

Save $108

United Airlines

Business Class

From ORD

Elite

Tallinn

Estonia • Aug 2026

85% AI deal score

$2,660

$1,244

Save $1,416

Scandinavian Airlines

Business Class

From ORD

Elite

Palma, Majorca

Spain • Sep 2026

85% AI deal score

$2,659

$1,278

Save $1,381

Scandinavian Airlines

Business Class

From ORD

Elite

Lower Prince's Quarter

Sint Maarten • Jul 2026

85% AI deal score

$1,345

$857

Save $488

Frontier

Business Class

From ORD

Elite

Kailua

United States • Jul 2026

85% AI deal score

$2,547

$1,869

Save $678

United Airlines

Business Class

From ORD

Elite

Budapest

Hungary • Aug 2026

84% AI deal score

$1,987

$1,269

Save $718

Scandinavian Airlines

Business Class

From ORD

Elite

Las Vegas

United States • Oct 2026

84% AI deal score

$889

$397

Save $492

Frontier

Business Class

From ORD

Elite

Florence

Italy • Jul 2026

84% AI deal score

$6,187

$4,827

Save $1,360

British Airways

Business Class

From ORD

Elite

Anguilla

Anguilla • Jul 2026

83% AI deal score

$1,604

$857

Save $747

Frontier

Business Class

From ORD

Elite

Port of Spain

Trinidad & Tobago • Jul 2026

83% AI deal score

$1,064

$910

Save $154

United

Business Class

From ORD

Elite

Rome

Italy • Aug 2026

83% AI deal score

$6,748

$4,922

Save $1,826

British Airways

Business Class

From ORD

Elite

Prague

Czechia • Nov 2026

82% AI deal score

$2,366

$1,261

Save $1,105

Scandinavian Airlines

Business Class

From ORD

Elite

Riga

Latvia • Nov 2026

82% AI deal score

$2,048

$1,282

Save $766

Scandinavian Airlines

Business Class

From ORD

Elite

Punta Cana

Dominican Republic • Aug 2026

82% AI deal score

$1,063

$730

Save $333

Frontier

Business Class

From ORD

Elite

Rome

Italy • Aug 2026

81% AI deal score

$2,472

$1,267

Save $1,205

Scandinavian Airlines

Business Class

From ORD

Elite

Florence

Italy • Aug 2026

79% AI deal score

$2,379

$1,252

Save $1,127

Scandinavian Airlines

Business Class

From ORD

Elite

Copenhagen

Denmark • Nov 2026

79% AI deal score

$2,661

$2,500

Save $161

Icelandair

Business Class

From ORD

Elite

Seattle

United States • Sep 2026

77% AI deal score

$673

$562

Save $111

Frontier

Business Class

From ORD

Elite

Dayton

United States • Jul 2026

77% AI deal score

$460

$419

Save $41

United Airlines

Business Class

From ORD

Elite

Denver

United States • Oct 2026

75% AI deal score

$470

$330

Save $140

Frontier

Business Class

From ORD

Elite

Cedar Rapids

United States • Jul 2026

73% AI deal score

$458

$419

Save $39

United Airlines

Business Class

From ORD

Elite

Puerto Plata

Dominican Republic • Nov 2026

72% AI deal score

$1,115

$938

Save $177

Delta

Business Class

From ORD

Elite

Los Angeles

United States • Sep 2026

71% AI deal score

$902

$887

Save $15

American

Business Class

From ORD

Elite

Santo Domingo

Dominican Republic • Oct 2026

69% AI deal score

$790

American

Business Class

From ORD

United States • Jul 2026

66% AI deal score

$772

$729

Save $43

United

Business Class

Booking Flights from Chicago: Frequently Asked Questions

Historically, several destinations from Chicago have been available for under $150. Across the trailing quarter, 8 destinations had median prices below this threshold. For example, flights to Manistee typically cost around $63, while flights to Provo had a median price of $73. Other affordable options include Kirksville at $79 and Decatur at $93.

Historically, flights from Chicago have offered access to a wide range of destinations. Across the trailing quarter, over 2,400 unique cities were observed. While the United States accounted for 37% of the observed destinations, Ireland followed with 9% and the United Kingdom with 6%.

Across the trailing 90 days, Dublin was historically the most frequently discounted destination from Chicago. London was also a popular choice, with a significant number of deals observed. Rome consistently ranked among the top three destinations for deals from Chicago.

Explore More Destinations from Chicago

Search more flights

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Cheap Flights from Chicago

Today’s best flight deals from Chicago

Unlock all 500+ flight deals from Chicago and get alerts when great deals appear

Origin Intelligence — 2,412 Destinations from Chicago Tracked

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

Compare nearby airports first

Jan

2-8 weeks in advance

United Airlines, American Airlines, Southwest Airlines, Deutsche Luft Hansa

From ~$30 direct / ~$64 roundtrip

Tue - Sat - Thu

Chicago main airports to depart from

Airports nearby Chicago used as alternative

Business & First Class Flight Deals from Chicago

Best Elite deals from Chicago

Alexandria

Mexico City

Pittsburgh

San Diego

St. Louis

Cleveland

Madison

San Diego

Cairo

Guadalajara

Mexico City

Lima

Honolulu

Kahului

Warsaw

Montreal

Cincinnati

Columbus

Minneapolis

Gdańsk

Guadalajara

Stockholm

Kauai

Oslo

Los Angeles

San Francisco

Milwaukee

Tallinn

Palma, Majorca

Lower Prince's Quarter

Kailua

Budapest

Las Vegas

Florence

Anguilla

Port of Spain

Rome

Prague

Riga

Punta Cana

Rome

Florence

Copenhagen

Seattle

Dayton

Denver

Cedar Rapids

Puerto Plata

Los Angeles

Santo Domingo

Peoria

Seattle

New York

Boston

Boston

Fort Lauderdale

Booking Flights from Chicago: Frequently Asked Questions

Which destinations from Chicago are under $150?

Which destinations from Chicago are under $150?