How far do most flights from Chicago go?

Historically, the majority of flights from Chicago are long-haul. In the trailing 90 days, 74% of observed destinations were long-haul. Medium-haul flights accounted for 12% of destinations, while short-haul flights made up 14% of the observed routes.

What's the cheapest destination from Chicago in Europe, Asia, and the Caribbean?

Across the trailing 90 days, the cheapest destination from Chicago within the United States was Manistee, with a median price of $63. For destinations in Canada, Toronto typically had a median price of $156. Flights to Mexico, such as Puebla, historically had a median price of $165.

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 44% savings compared to the annual median average price of $882. April was the second cheapest month, 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 6 days ago

400 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Jul 5, 2026.)

All Deals

⌛ Last-Minute

🔥 Trending

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Today’s best flight deals from Chicago

Explore current cheapest deals departing from Chicago

One-way

Sort by: Cheapest

RFD

Orlando

United States • Oct 2026

$102

$28

One-way

RFD

Fort Lauderdale

United States • Oct 2026

$103

$30

One-way

RFD

Nashville

United States • Aug 2026

$70

$33

One-way

RFD

Tampa

United States • Oct 2026

$94

$38

One-way

ORD

Washington, D.C.

United States • Oct 2026

$79

$44

One-way

RFD

Phoenix

United States • Aug 2026

$105

$45

One-way

ORD

Denver

United States • Sep 2026

$85

$46

One-way

ORD

Houston

United States • Aug 2026

$98

$49

One-way

MDW

Destin

United States • Aug 2026

$87

$49

One-way

MDW

Knoxville

United States • Aug 2026

$92

$51

One-way

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

Flights from Chicago: Overview

Insights for flights from Chicago

Travelers from Chicago can reach a substantial number of destinations, with recent fare data showing access to 2,412 unique cities 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 like Ireland and the United Kingdom.

For those seeking cheap flights from Chicago, the most economical fares right now include trips to Dallas for $50, Atlanta for $50, and Fort Lauderdale for $55. These prices represent the lowest available roundtrip fares to these destinations, offering budget-friendly options for both domestic business and leisure travel.

The route mix from Chicago is predominantly long-distance, with 74% of recent routes classified as long-haul. 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 extensive national and international travel.

Among recent fares, Dublin is the most frequently discounted destination from Chicago, followed by London and Rome. These cities consistently appear in recent fare observations, suggesting they are popular choices for travelers departing from Chicago and often feature competitive pricing.

When considering direct flights from Chicago, about 22.8% of recent fares are non-stop. This indicates that while direct options are available, a significant portion of flights from Chicago involve connections, making it a connecting-dominant origin for many routes.

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

Wed, Jul 8

⌛ Last-Minute

MDW - Anchorage

Chicago (MDW) - Anchorage (ANC)

Deutsche Luft Hansa

$845

$494

One-way

Thu, Jul 9

⌛ Last-Minute

MDW - Reykjavik

Chicago (MDW) - Reykjavik (KEF)

Virgin Atlantic

$889

$419

One-way

Mon, Jul 6

⌛ Last-Minute

MDW - Kauai

Chicago (MDW) - Kauai (LIH)

Southwest Airlines

$980

$593

One-way

Sun, Jul 5

⌛ Last-Minute

MDW - Rio de Janeiro

Chicago (MDW) - Rio de Janeiro (GIG)

LATAM Chile

$1,170

$776

One-way

Fri, Jul 10

⌛ Last-Minute

MDW - Recife

Chicago (MDW) - Recife (REC)

Deutsche Luft Hansa

$1,316

$881

One-way

Tue, Jul 14

⌛ Last-Minute

MDW - Bangkok

Chicago (MDW) - Bangkok (BKK)

Deutsche Luft Hansa

$1,488

$1,081

One-way

Most popular destinations to fly from Chicago

Dublin

TOP

Ireland • Dec 2026

from

$329

Bengaluru

TOP

India • Mar 2027

from

$803

Kigali

TOP

Rwanda • Aug 2026

from

$1,026

Reykjavik

TOP

Iceland • Sep 2026

from

$322

Naples

TOP

Italy • Dec 2026

from

$739

Manila

TOP

Philippines • Mar 2027

from

$846

Biggest price drops on international destinations from Chicago

-44%

MDW - Kigali

$1,826 → $1,026

-52%

ORD - New Delhi

$1,448 → $691

-42%

MDW - Linköping

$1,367 → $792

-33%

MDW - Entebbe

$1,665 → $1,112

Popular Airports from Chicago

Chicago airport insights

🎯 Booking tip

Compare nearby airports first

Flights from RFD start at $29, while flights from ORD start at $22.

📅 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 and a low-cost airline offer many domestic and international flight options.

💸 Cheapest deals found

From ~$30 direct / ~$50 roundtrip

Ultra-low fares cluster on routes to Fort Lauderdale, Dallas, and Atlanta in the United States.

🗓️ 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

Best Elite deals from Chicago

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

From ORD

Elite

Amsterdam

Netherlands • Oct 2026

96% AI deal score

$13,960

$4,869

Save $9,091

British Airways

Business Class

From ORD

Elite

Cleveland

United States • Aug 2026

95% AI deal score

$645

$337

Save $308

United Airlines

Business Class

From ORD

Elite

Cairo

Egypt • Nov 2026

95% AI deal score

$12,307

$4,707

Save $7,600

British Airways

Business Class

From ORD

Elite

Mexico City

Mexico • Sep 2026

94% AI deal score

$1,612

$555

Save $1,057

Aeroméxico

Business Class

From ORD

Elite

Pittsburgh

United States • Aug 2026

94% AI deal score

$677

$357

Save $320

United Airlines

Business Class

From ORD

Elite

Milwaukee

United States • Aug 2026

94% AI deal score

$682

$397

Save $285

United Airlines

Business Class

From ORD

Elite

San Diego

United States • Aug 2026

94% AI deal score

$1,235

$727

Save $508

Alaska Airlines, Inc.

Business Class

From ORD

Elite

San Diego

United States • Sep 2026

93% AI deal score

$1,270

$727

Save $543

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Grand Rapids

United States • Aug 2026

93% AI deal score

$634

$376

Save $258

United Airlines

Business Class

From ORD

Elite

Santa Cruz de la Sierra

Bolivia • Aug 2026

92% AI deal score

$3,067

$1,565

Save $1,502

Copa Airlines

Business Class

From ORD

Elite

Minneapolis

United States • Aug 2026

92% AI deal score

$550

$337

Save $213

United Airlines

Business Class

From ORD

Elite

Indianapolis

United States • Aug 2026

92% AI deal score

$545

$357

Save $188

United Airlines

Business Class

From ORD

Elite

Honolulu

United States • Mar 2027

92% AI deal score

$3,026

$1,910

Save $1,116

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Kahului

United States • Mar 2027

92% AI deal score

$3,021

$1,952

Save $1,069

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Riga

Latvia • Dec 2026

91% AI deal score

$2,158

$1,184

Save $974

Scandinavian Airlines

Business Class

From ORD

Elite

Oslo

Norway • Dec 2026

91% AI deal score

$2,308

$1,244

Save $1,064

Scandinavian Airlines

Business Class

From ORD

Elite

Stockholm

Sweden • Dec 2026

91% AI deal score

$2,273

$1,245

Save $1,028

Scandinavian Airlines

Business Class

From ORD

Elite

Mexico City

Mexico • Sep 2026

91% AI deal score

$1,135

$721

Save $414

Aeroméxico

Business Class

From ORD

Elite

Cincinnati

United States • Jul 2026

91% AI deal score

$551

$355

Save $196

United Airlines

Business Class

From ORD

Elite

Columbus

United States • Aug 2026

91% AI deal score

$515

$358

Save $157

United Airlines

Business Class

From ORD

Elite

Oslo

Norway • Oct 2026

90% AI deal score

$2,273

$1,193

Save $1,080

Scandinavian Airlines

Business Class

From ORD

Elite

Zürich

Switzerland • Nov 2026

90% AI deal score

$2,602

$1,198

Save $1,404

Scandinavian Airlines

Business Class

From ORD

Elite

Lima

Peru • Mar 2027

90% AI deal score

$4,022

$1,625

Save $2,397

Copa Airlines

Business Class

From ORD

Elite

Montevideo

Uruguay • Dec 2026

90% AI deal score

$2,826

$1,813

Save $1,013

Avianca

Business Class

From ORD

Elite

Madison

United States • Jul 2026

90% AI deal score

$569

$419

Save $150

United Airlines

Business Class

From ORD

Elite

Munich

Germany • Nov 2026

89% AI deal score

$2,672

$1,284

Save $1,388

Scandinavian Airlines

Business Class

From ORD

Elite

Oslo

Norway • Nov 2026

89% AI deal score

$4,468

$2,473

Save $1,995

Icelandair

Business Class

From MDW

Elite

Miami

United States • Aug 2026

89% AI deal score

$4,877

$994

Save $3,883

Deutsche Luft Hansa, +1

Business Class

From ORD

Elite

Amsterdam

Netherlands • Oct 2026

88% AI deal score

$2,730

$1,248

Save $1,482

Scandinavian Airlines

Business Class

From ORD

Elite

Tenerife

Spain • Nov 2026

88% AI deal score

$2,536

$1,286

Save $1,250

Scandinavian Airlines

Business Class

From ORD

Elite

Memphis

United States • Aug 2026

88% AI deal score

$554

$377

Save $177

United Airlines

Business Class

From ORD

Elite

Athens

Greece • Oct 2026

87% AI deal score

$2,716

$1,245

Save $1,471

Scandinavian Airlines

Business Class

From ORD

Elite

Copenhagen

Denmark • Feb 2027

87% AI deal score

$1,633

$1,252

Save $381

Scandinavian Airlines

Business Class

From MDW

Elite

San Juan

United States • Oct 2026

87% AI deal score

$1,847

$666

Save $1,181

Frontier

Business Class

From MDW

Elite

Saint Thomas

United States • Aug 2026

87% AI deal score

$2,445

$1,505

Save $940

Delta

Business Class

From ORD

Elite

Brussels

Belgium • Oct 2026

86% AI deal score

$1,860

$1,155

Save $705

Scandinavian Airlines

Business Class

From ORD

Elite

Helsinki

Finland • Nov 2026

86% AI deal score

$2,080

$1,195

Save $885

Scandinavian Airlines

Business Class

From ORD

Elite

Paris

France • Oct 2026

86% AI deal score

$2,578

$1,195

Save $1,383

Scandinavian Airlines

Business Class

From ORD

Elite

Stockholm

Sweden • Feb 2027

86% AI deal score

$3,640

$2,385

Save $1,255

Icelandair

Business Class

From ORD

Elite

Louisville

United States • Aug 2026

86% AI deal score

$596

$424

Save $172

United Airlines

Business Class

From ORD

Elite

London

United Kingdom • Oct 2026

85% AI deal score

$2,279

$1,247

Save $1,032

Scandinavian Airlines

Business Class

From ORD

Elite

Prague

Czechia • Dec 2026

85% AI deal score

$2,591

$1,252

Save $1,339

Scandinavian Airlines

Business Class

From ORD

Elite

Anguilla

Anguilla • Jul 2026

85% AI deal score

$1,750

$853

Save $897

Frontier

Business Class

From MDW

Elite

Punta Cana

Dominican Republic • Aug 2026

85% AI deal score

$1,460

$796

Save $664

Frontier

Business Class

From ORD

Elite

St. Louis

United States • Aug 2026

85% AI deal score

$536

$396

Save $140

United Airlines

Business Class

From ORD

Elite

Cedar Rapids

United States • Jul 2026

85% AI deal score

$568

$419

Save $149

United Airlines

Business Class

From MDW

Elite

San Juan

United States • Aug 2026

85% AI deal score

$1,559

$956

Save $603

Delta

Business Class

From ORD

Elite

Frankfurt

Germany • Mar 2027

84% AI deal score

$2,400

$1,295

Save $1,105

Scandinavian Airlines

Business Class

From ORD

Elite

Las Vegas

United States • Sep 2026

84% AI deal score

$996

$430

Save $566

Frontier

Business Class

From MDW

Elite

San Francisco

United States • Aug 2026

84% AI deal score

$1,113

$516

Save $597

Frontier

Business Class

From ORD

Elite

Florence

Italy • Aug 2026

84% AI deal score

$8,068

$4,826

Save $3,242

British Airways

Business Class

From ORD

Elite

Milan

Italy • Oct 2026

83% AI deal score

$2,376

$1,195

Save $1,181

Scandinavian Airlines

Business Class

From MDW

Elite

Los Angeles

United States • Aug 2026

83% AI deal score

$1,012

$510

Save $502

Frontier

Business Class

From ORD

Elite

Seville

Spain • Dec 2026

82% AI deal score

$2,666

$1,185

Save $1,481

Scandinavian Airlines

Business Class

From ORD

Elite

Lima

Peru • Sep 2026

82% AI deal score

$2,598

$1,190

Save $1,408

Aeroméxico

Business Class

From ORD

Elite

Barcelona

Spain • Oct 2026

82% AI deal score

$2,506

$1,195

Save $1,311

Scandinavian Airlines

Business Class

From ORD

Elite

Lisbon

Portugal • Nov 2026

82% AI deal score

$2,465

$1,299

Save $1,166

Scandinavian Airlines

Business Class

From ORD

Elite

Quito

Ecuador • Sep 2026

82% AI deal score

$7,449

$1,998

Save $5,451

Avianca

Business Class

From ORD

Elite

Kailua

United States • Aug 2026

82% AI deal score

$2,564

$1,946

Save $618

United Airlines

Business Class

From ORD

Elite

Valencia

Spain • Aug 2026

82% AI deal score

$6,080

$4,937

Save $1,143

British Airways

Business Class

From ORD

Elite

Geneva

Switzerland • Nov 2026

81% AI deal score

$2,414

$1,242

Save $1,172

Scandinavian Airlines

Business Class

From ORD

Elite

Florence

Italy • Oct 2026

81% AI deal score

$2,600

$1,244

Save $1,356

Scandinavian Airlines

Business Class

From ORD

Elite

Rome

Italy • Feb 2027

81% AI deal score

$2,609

$1,256

Save $1,353

Scandinavian Airlines

Business Class

From ORD

Elite

Venice

Italy • Feb 2027

81% AI deal score

$2,620

$1,297

Save $1,323

Scandinavian Airlines

Business Class

From ORD

Elite

Orlando

United States • Sep 2026

81% AI deal score

$678

$406

Save $272

Frontier

Business Class

From ORD

Elite

Kingston

Jamaica • Sep 2026

81% AI deal score

$821

$758

Save $63

American

Business Class

From MDW

Elite

Seattle

United States • Dec 2026

81% AI deal score

$1,112

$857

Save $255

Delta

Business Class

From ORD

Elite

Moline

United States • Aug 2026

81% AI deal score

$501

$419

Save $82

United Airlines

Business Class

From ORD

Elite

Saint Andrew Parish

Dominica • Sep 2026

81% AI deal score

$1,587

$1,252

Save $335

Contour Airlines, +1

Business Class

From MDW

Elite

Montego Bay

Jamaica • Sep 2026

81% AI deal score

$1,496

$762

Save $734

Frontier

Business Class

From ORD

Elite

Willemstad

Curaçao • Oct 2026

79% AI deal score

$1,763

$1,487

Save $276

American

Business Class

From ORD

Elite

Cartagena

Colombia • Aug 2026

78% AI deal score

$1,161

$925

Save $236

American

Business Class

From ORD

Elite

Tortola

British Virgin Islands • Aug 2026

78% AI deal score

$1,640

$1,398

Save $242

American

Business Class

From ORD

Elite

Dayton

United States • Aug 2026

77% AI deal score

$463

$419

Save $44

United Airlines

Business Class

From ORD

Elite

Budapest

Hungary • Nov 2026

76% AI deal score

$2,350

$1,215

Save $1,135

Scandinavian Airlines

Business Class

From ORD

Elite

Vienna

Austria • Oct 2026

76% AI deal score

$2,384

$1,275

Save $1,109

Scandinavian Airlines

Business Class

From MDW

Elite

San Francisco

United States • Nov 2026

75% AI deal score

$1,439

$1,235

Save $204

Delta

Business Class

From MDW

Elite

New Orleans

United States • Oct 2026

75% AI deal score

$1,059

$483

Save $576

Frontier

Business Class

From MDW

Elite

Santo Domingo

Dominican Republic • Sep 2026

75% AI deal score

$994

$908

Save $86

Delta

Business Class

From ORD

Elite

Santiago de Chile

Chile • Oct 2026

74% AI deal score

$1,845

Avianca

Business Class

From ORD

Colombia • Nov 2026

72% AI deal score

$818

Avianca

Business Class

From ORD

Elite

Appleton

United States • Aug 2026

72% AI deal score

$436

$419

Save $17

United Airlines

Business Class

From ORD

Elite

Aruba

Aruba • Jul 2026

72% AI deal score

$1,451

American

Business Class

From ORD

Elite

Grand Cayman

Cayman Islands • Jan 2027

72% AI deal score

$1,301

$1,151

Save $150

American

Business Class

From ORD

Elite

Bogotá

Colombia • Sep 2026

71% AI deal score

$861

United

Business Class

From MDW

Elite

New York

United States • Aug 2026

71% AI deal score

$658

$504

Save $154

Frontier

Business Class

From MDW

Elite

Washington, D.C.

United States • Aug 2026

70% AI deal score

$611

$488

Save $123

Frontier

Business Class

From ORD

Elite

New York

United States • Aug 2026

69% AI deal score

$496

$451

Save $45

American

Business Class

From ORD

Elite

New York

United States • Aug 2026

67% AI deal score

$496

$451

Save $45

American

Business Class

From ORD

Elite

Seattle

United States • Sep 2026

66% AI deal score

$758

American

Business Class

From MDW

Elite

Orlando

United States • Aug 2026

66% AI deal score

$809

$767

Save $42

Delta

Business Class

From MDW

Elite

New Orleans

United States • Aug 2026

65% AI deal score

$694

$641

Save $53

Delta

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.

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