Chicago → Africa(15)
Accra
Ghana
17 hr 30 min (1 Stop)
Addis Ababa
Ethiopia
16 hr 30 min (1 Stop)
Cairo
Egypt
14 hr 30 min (1 Stop)
Cape Town
South Africa
20 hr 30 min (1 Stop, typical via Johannesburg or Addis Ababa)
Casablanca
Morocco
13 hr 30 min (1 Stop)
Dakar
Senegal
16 hr 30 min (1 Stop) — typical fastest option with one connection
Johannesburg
South Africa
18 hr 30 min (1 Stop)
Kigali
Rwanda
20 hr 30 min (2 Stops typical)
Lagos
Nigeria
20 hr 30 min (1 Stop)
Luxor
Egypt
18 hr 30 min (2 Stops typical)
Marrakech
Morocco
13 hr 30 min (1 Stop)
Mauritius
Mauritius
20 hr 30 min (1-2 Stops)
Nairobi
Kenya
17 hr 30 min (1 Stop)
Seychelles
Seychelles
20 hr+ (2+ Stops)
Zanzibar
Tanzania
22 hr - 28 hr (2+ Stops)
Chicago → Caribbean(10)
Aruba
Aruba
5 hr 30 min (1 Stop)
Barbados
Barbados
7 hr 30 min (1 Stop)
Bermuda
Bermuda
2 hr 30 min (Direct)
Cancún
Mexico
3 hr 30 min (Direct)
Curaçao
Curaçao
8 hr 30 min (1 Stop)
Havana
Cuba
3 hr 30 min (Direct)
Montego Bay
Jamaica
3 hr 45 min (Direct)
Nassau
Bahamas
3 hr 30 min (1 Stop)
Punta Cana
Dominican Republic
4 hr 30 min (Direct)
San Juan
Puerto Rico
3 hr 50 min (Direct)
Chicago → Central America(4)
Chicago → Central Asia(11)
Almaty
Kazakhstan
19 hr 30 min (1 Stop)
Baku
Azerbaijan
17 hr 30 min (1 Stop)
Delhi
India
14 hr 30 min (1 Stop) — typical fastest option with one connection
Goa
India
20 hr 30 min (1-2 Stops)
Jaipur
India
18 hr 30 min (1 Stop)
Kathmandu
Nepal
18 hr 30 min (1 Stop, typical via Middle East or South/Southeast Asia hub)
Mumbai
India
16 hr 30 min (1 Stop)
Tashkent
Uzbekistan
18 hr 30 min (1 Stop)
Tbilisi
Georgia
18 hr 30 min (1-2 Stops)
Varanasi
India
22 hr 30 min (1-2 Stops)
Yerevan
Armenia
17 hr 30 min (1 Stop)
Chicago → East Asia(14)
Beijing
China
13 hr 30 min (1 Stop typical; occasional nonstop ~13 hr)
Busan
South Korea
16 hr 30 min (1 Stop) — typical fastest option with one connection
Chengdu
China
14 hr 30 min (1 Stop)
Guangzhou
China
14 hr 30 min (1 Stop)
Hiroshima
Japan
16 hr 30 min (1 Stop)
Hong Kong
China
15 hr 30 min (1 Stop typical; ~16-17 hr with connection)
Kyoto
Japan
14 hr 30 min (1 Stop, via Tokyo or Osaka)
Macau
China
17 hr 30 min (1 Stop)
Osaka
Japan
13 hr 30 min (1 Stop)
Sapporo
Japan
14 hr 30 min (1 Stop)
Seoul
South Korea
14 hr 30 min (Direct)
Shanghai
China
14 hr 30 min (1 Stop typical; ~13 hr nonstop when available)
Taipei
Taiwan
16 hr 30 min (1 Stop)
Tokyo
Japan
13 hr 30 min (Direct)
Chicago → Europe(58)
Amalfi Coast
Italy
11 hr 30 min (1 Stop)
Amsterdam
Netherlands
8 hr 30 min (Direct)
Antalya
Turkey
13 hr 30 min (1 Stop)
Athens
Greece
11 hr 30 min (1 Stop)
Barcelona
Spain
9 hr 30 min (1 Stop)
Bergen
Norway
12 hr 30 min (1 Stop)
Berlin
Germany
9 hr 30 min (1 Stop)
Bratislava
Slovakia
13 hr 30 min (1 Stop)
Bruges
Belgium
9 hr 30 min (1 Stop)
Brussels
Belgium
9 hr 30 min (Direct)
Bucharest
Romania
14 hr 30 min (1 Stop)
Budapest
Hungary
10 hr 30 min (1 Stop)
Copenhagen
Denmark
9 hr 30 min (Direct)
Corfu
Greece
14 hr 30 min (2 Stops typical)
Crete
Greece
14 hr 30 min (1 Stop)
Dublin
Ireland
8 hr 30 min (Direct)
Dubrovnik
Croatia
13 hr 30 min (1 Stop)
Edinburgh
United Kingdom
9 hr 30 min (1 Stop)
Florence
Italy
13 hr 30 min (1 Stop)
Frankfurt
Germany
9 hr 30 min (Direct)
Gothenburg
Sweden
11 hr 30 min (1 Stop)
Helsinki
Finland
10 hr 30 min (1 Stop)
Ibiza
Spain
13 hr 30 min (1 Stop minimum — common connections via Madrid, Barcelona, London, or Frankfurt)
Istanbul
Turkey
11 hr 30 min (1 Stop)
Kraków
Poland
10 hr 30 min (1 Stop)
Lisbon
Portugal
9 hr 45 min (1 Stop)
Ljubljana
Slovenia
14 hr 30 min (1-2 Stops typical, via hubs like Frankfurt, Vienna, Munich, or Zurich)
London
United Kingdom
8 hr 30 min (Direct)
Madrid
Spain
9 hr 30 min (Direct)
Málaga
Spain
11 hr 30 min (1 Stop)
Malta
Malta
14 hr 30 min (1-2 Stops)
Milan
Italy
9 hr 45 min (Direct)
Monaco
Monaco
10 hr 30 min (1 Stop)
Munich
Germany
9 hr 30 min (Direct)
Mykonos
Greece
14 hr 30 min (1 Stop)
Naples
Italy
11 hr 30 min (1 Stop)
Nice
France
10 hr 30 min (1 Stop)
Oslo
Norway
9 hr 30 min (1 Stop)
Paris
France
8 hr 30 min (Direct)
Porto
Portugal
10 hr 30 min (1 Stop)
Prague
Czech Republic
10 hr 30 min (1 Stop)
Reykjavik
Iceland
7 hr 15 min (Direct)
Rhodes
Greece
14 hr 30 min (1-2 Stops)
Riga
Latvia
13 hr 30 min (1 Stop)
Rome
Italy
10 hr 30 min (1 Stop typical, via hub)
Salzburg
Austria
13 hr 30 min (1 Stop)
Santorini
Greece
14 hr 30 min (1 Stop minimum — typically via Athens ATH or a European hub)
Seville
Spain
13 hr 30 min (1 Stop)
Sofia
Bulgaria
13 hr 30 min (1 Stop)
Split
Croatia
13 hr 30 min (1 Stop)
Stockholm
Sweden
9 hr 45 min (1 Stop)
Tallinn
Estonia
13 hr 30 min (1 Stop)
Thessaloniki
Greece
14 hr 30 min (1 Stop)
Venice
Italy
10 hr 30 min (1 Stop)
Vienna
Austria
10 hr 15 min (1 Stop)
Vilnius
Lithuania
14 hr 30 min (1 Stop)
Warsaw
Poland
10 hr 15 min (1 Stop)
Zurich
Switzerland
9 hr 30 min (Direct)
Chicago → Middle East(9)
Abu Dhabi
UAE
14 hr 30 min (1 Stop typical, via Europe or Middle East)
Amman
Jordan
13 hr 30 min (1 Stop)
Beirut
Lebanon
14 hr 30 min (1 Stop)
Doha
Qatar
13 hr 45 min (1 Stop)
Dubai
UAE
14 hr 30 min (1 Stop typical, via Europe or Middle East)
Jeddah
Saudi Arabia
16 hr 30 min (1 Stop)
Muscat
Oman
17 hr 30 min (1 Stop)
Riyadh
Saudi Arabia
16 hr 30 min (1 Stop)
Tel Aviv
Israel
12 hr 30 min (1 Stop typical; rare charters may be direct)
Chicago → North America(16)
Boston
United States
2 hr 30 min (Direct)
Denver
United States
2 hr 30 min (Direct)
Honolulu
United States
9 hr 30 min (Direct)
Las Vegas
United States
3 hr 45 min (Direct)
Los Angeles
United States
3 hr 55 min (Direct)
Maui
United States
9 hr 30 min (Direct)
Mexico City
Mexico
4 hr 30 min (Direct)
Miami
United States
3 hr 10 min (Direct)
Montréal
Canada
2 hr 10 min (Direct)
New Orleans
United States
2 hr 30 min (Direct)
New York
United States
2 hr 20 min (Direct)
San Francisco
United States
4 hr 30 min (Direct)
Seattle
United States
4 hr 15 min (Direct)
Toronto
Canada
1 hr 20 min (Direct)
Vancouver
Canada
4 hr 30 min (Direct)
Washington D.C.
United States
2 hr 10 min (Direct)
Chicago → Oceania(10)
Auckland
New Zealand
17 hr 30 min (1 Stop, e.g. via LAX or SFO)
Bora Bora
French Polynesia
16 hr 30 min (2+ Stops)
Brisbane
Australia
20 hr 30 min (1 Stop)
Christchurch
New Zealand
20 hr 30 min (2 Stops typical)
Fiji
Fiji
18 hr 30 min (1 Stop)
Melbourne
Australia
19 hr 30 min (1 Stop, typical via LAX or SFO)
Perth
Australia
22 hr 30 min (1-2 Stops)
Queenstown
New Zealand
20 hr 30 min (2+ Stops) — typical fastest option with connections via Auckland or Sydney
Sydney
Australia
19 hr 30 min (1 Stop, via LAX or SFO typically)
Tahiti
French Polynesia
~13-16 hr (1-2 Stops, e.g. via LAX or PPG)
Chicago → South America(10)
Bogotá
Colombia
7 hr 30 min (Direct)
Buenos Aires
Argentina
13 hr 30 min (1 Stop)
Cartagena
Colombia
9 hr 30 min (1 Stop)
Cusco
Peru
16 hr 30 min (2 Stops typical)
Lima
Peru
8 hr 30 min (1 Stop)
Medellín
Colombia
9 hr 30 min (1 Stop)
Quito
Ecuador
11 hr 30 min (1 Stop)
Rio de Janeiro
Brazil
12 hr 30 min (1 Stop)
Santiago
Chile
13 hr 30 min (1 Stop)
São Paulo
Brazil
10 hr 30 min (1 Stop typical, via Miami or New York)
Chicago → Southeast Asia(18)
Bali
Indonesia
20 hr 30 min (1-2 Stops)
Bangkok
Thailand
20 hr 30 min (1 Stop)
Chiang Mai
Thailand
20 hr 30 min (2 Stops typical)
Colombo
Sri Lanka
20 hr 30 min (1 Stop)
Da Nang
Vietnam
20 hr 30 min (1 Stop, typical via Seoul, Tokyo, or Taipei)
Hanoi
Vietnam
20 hr 30 min (1 Stop)
Ho Chi Minh City
Vietnam
20 hr 30 min (1 Stop)
Jakarta
Indonesia
20 hr 30 min (1 Stop)
Koh Samui
Thailand
20 hr 30 min (2 Stops typical)
Krabi
Thailand
22 hr (2+ Stops)
Kuala Lumpur
Malaysia
20 hr 30 min (1 Stop)
Langkawi
Malaysia
22 hr (2+ Stops)
Maldives
Maldives
20 hr 30 min (2 Stops)
Manila
Philippines
17 hr 30 min (1 Stop)
Penang
Malaysia
20 hr 30 min (2 Stops typical)
Phuket
Thailand
22 hr 30 min (2 Stops typical)
Siem Reap
Cambodia
20 hr+ (2+ Stops)
Singapore
Singapore
18 hr 30 min (1 Stop)
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Finding Cheap Flights from Chicago in 2026
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