Best Trips from Chicago — Cheap Flights & Travel Windows April 2026 | GoNow

Explore

Top Windows from Chicago

51 destinations ranked by value + timing

Kyoto

Japan

Kyoto

✈️ Fares found from $746

Rome

Italy

Rome

✈️ Fares found from $674

Istanbul

Turkey

Istanbul

🌷Istanbul Tulip Festival Currency +17%

✈️ Fares found from $667

Bangkok

Thailand

Bangkok

💦Songkran Water Festival 32% below avg

✈️ Fares found from $542

Chiang Mai

Thailand

Chiang Mai

waterSongkran Water Festival 32% below avg

✈️ Fares found from $587

Seoul

South Korea

Seoul

Cherry blossom season 22% below avg

✈️ Fares found from $660

Marrakech

Morocco

Marrakech

🌺Ideal weather before summer heat 21% below avg

✈️ Fares found from $513

Amsterdam

Netherlands

Amsterdam

🌷Tulip season at Keukenhof 29% below avg

✈️ Fares found from $385

Paris

France

Paris

🌷Paris in spring 18% below avg

✈️ Fares found from $457

Vancouver

Canada

Vancouver

Cherry Blossom Festival 37% below avg

✈️ Fares found from $222

Lisbon

Portugal

Lisbon

Perfect spring weather 32% below avg

✈️ Fares found from $421

Barcelona

Spain

Barcelona

Whale watching season

✈️ Fares found from $566

Bogota

Colombia

Bogota

📚Bogota International Book Fair

✈️ Fares found from $491

London

United Kingdom

London

🌺Chelsea Flower Show

✈️ Fares found from $463

Sydney

Australia

Sydney

💡Vivid Sydney 38% below avg

✈️ Fares found from $677

Cancun

Mexico

Cancun

✈️ Fares found from $183

Rio de Janeiro

Brazil

Rio de Janeiro

✈️ Fares found from $343

Santorini

Greece

Santorini

Shoulder Season Deals

✈️ Fares found from $803

Prague

Czech Republic

Prague

🌷Prague Spring

✈️ Fares found from $591

Mumbai

India

Mumbai

✈️ Fares found from $487

Lima

Peru

Lima

✈️ Fares found from $369

Honolulu

USA

Honolulu

✈️ Fares found from $234

Cartagena

Colombia

Cartagena

✈️ Fares found from $146

Hanoi

Vietnam

Hanoi

✈️ Fares found from $499

Dubrovnik

Croatia

Dubrovnik

🏰Game of Thrones Touring Season

✈️ Fares found from $725

Mexico City

Mexico

Mexico City

✈️ Fares found from $198

Hong Kong

China

Hong Kong

✈️ Fares found from $608

Tokyo

Japan

Tokyo

✈️ Fares found from $749

Santiago

Chile

Santiago

✈️ Fares found from $497

Cairo

Egypt

Cairo

✈️ Fares found from $834

Las Vegas

USA

Las Vegas

✈️ Fares found from $128

Dubai

UAE

Dubai

✈️ Fares found from $448

Buenos Aires

Argentina

Buenos Aires

✈️ Fares found from $507

Osaka

Japan

Osaka

✈️ Fares found from $703

Cape Town

South Africa

Cape Town

✈️ Fares found from $841

Athens

Greece

Athens

✈️ Fares found from $758

Havana

Cuba

Havana

✈️ Fares found from $287

Ho Chi Minh City

Vietnam

Ho Chi Minh City

✈️ Fares found from $541

Nashville

USA

Nashville

musicCMA Fest 23% below avg

✈️ Fares found from $116

Bali

Indonesia

Bali

✈️ Fares found from $703

Budapest

Hungary

Budapest

✈️ Fares found from $732

Auckland

New Zealand

Auckland

✈️ Fares found from $1268

Vienna

Austria

Vienna

✈️ Fares found from $462

Berlin

Germany

Berlin

✈️ Fares found from $344

Medellin

Colombia

Medellin

✈️ Fares found from $179

Melbourne

Australia

Melbourne

✈️ Fares found from $930

Singapore

Singapore

Singapore

✈️ Fares found from $621

Copenhagen

Denmark

Copenhagen

✈️ Fares found from $386

Edinburgh

Scotland

Edinburgh

✈️ Fares found from $699

Dublin

Ireland

Dublin

✈️ Fares found from $601

Reykjavik

Iceland

Reykjavik

✈️ Fares found from $505