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

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Top Windows from Chicago

53 destinations ranked by value + timing

Cape Town

South Africa

Cape Town

✈️ Fares found from $791

Seoul

South Korea

Seoul

Cherry blossom season 22% below avg

✈️ Fares found from $660

Kyoto

Japan

Kyoto

Cherry Blossom Season 20% below avg

✈️ Fares found from $746

Rome

Italy

Rome

⛪Easter at the Vatican

✈️ Fares found from $674

Marrakech

Morocco

Marrakech

🌺Ideal weather before summer heat 21% below avg

✈️ Fares found from $513

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

Istanbul

Turkey

Istanbul

🌷Istanbul Tulip Festival 12% below avg Currency +17%

✈️ Fares found from $608

Osaka

Japan

Osaka

✈️ Fares found from $703

Phuket

Thailand

Phuket

💦Songkran Water Festival 31% below avg

✈️ Fares found from $608

Honolulu

USA

Honolulu

✈️ Fares found from $234

Lisbon

Portugal

Lisbon

Perfect spring weather 34% below avg

✈️ Fares found from $411

Amsterdam

Netherlands

Amsterdam

🌷Tulip season at Keukenhof 20% below avg

✈️ Fares found from $430

Lima

Peru

Lima

✈️ Fares found from $369

Vancouver

Canada

Vancouver

Cherry Blossom Festival 40% below avg

✈️ Fares found from $211

London

United Kingdom

London

🌺Chelsea Flower Show

✈️ Fares found from $489

Barcelona

Spain

Barcelona

Whale watching season 10% below avg

✈️ Fares found from $520

Prague

Czech Republic

Prague

🌷Prague Spring

✈️ Fares found from $752

Dubrovnik

Croatia

Dubrovnik

🏰Game of Thrones Touring Season

✈️ Fares found from $743

Santorini

Greece

Santorini

Shoulder Season Deals 28% below avg

✈️ Fares found from $521

Hanoi

Vietnam

Hanoi

✈️ Fares found from $513

Mexico City

Mexico

Mexico City

✈️ Fares found from $193

Paris

France

Paris

🌷Paris in spring 27% below avg

✈️ Fares found from $407

Bogota

Colombia

Bogota

📚Bogota International Book Fair

✈️ Fares found from $491

Hong Kong

China

Hong Kong

✈️ Fares found from $557

Tokyo

Japan

Tokyo

✈️ Fares found from $754

Santiago

Chile

Santiago

✈️ Fares found from $557

Cairo

Egypt

Cairo

✈️ Fares found from $834

Siem Reap

Cambodia

Siem Reap

✈️ Fares found from $692

Mumbai

India

Mumbai

✈️ Fares found from $574

Dubai

UAE

Dubai

✈️ Fares found from $666

Las Vegas

USA

Las Vegas

✈️ Fares found from $178

Havana

Cuba

Havana

✈️ Fares found from $287

Cancun

Mexico

Cancun

✈️ Fares found from $183

Sydney

Australia

Sydney

💡Vivid Sydney 51% below avg

✈️ Fares found from $539

Ho Chi Minh City

Vietnam

Ho Chi Minh City

✈️ Fares found from $662

Nashville

USA

Nashville

✈️ Fares found from $143

Buenos Aires

Argentina

Buenos Aires

✈️ Fares found from $507

Melbourne

Australia

Melbourne

✈️ Fares found from $855

Rio de Janeiro

Brazil

Rio de Janeiro

✈️ Fares found from $805

Auckland

New Zealand

Auckland

✈️ Fares found from $775

Cartagena

Colombia

Cartagena

✈️ Fares found from $146

Singapore

Singapore

Singapore

✈️ Fares found from $498

Budapest

Hungary

Budapest

✈️ Fares found from $714

Bali

Indonesia

Bali

✈️ Fares found from $718

Athens

Greece

Athens

✈️ Fares found from $438

Medellin

Colombia

Medellin

✈️ Fares found from $179

Berlin

Germany

Berlin

✈️ Fares found from $340

Vienna

Austria

Vienna

✈️ Fares found from $389

Copenhagen

Denmark

Copenhagen

✈️ Fares found from $386

Reykjavik

Iceland

Reykjavik

✈️ Fares found from $509

Dublin

Ireland

Dublin

✈️ Fares found from $601

Edinburgh

Scotland

Edinburgh

✈️ Fares found from $699