Departing Chicago

Cheap Flights from Chicago

The cheapest fares we found leaving Chicago right now are Atlanta at $67, Denver at $89 and Las Vegas at $116 round trip. Below are 352 destinations we hold current fares for, cheapest first, with the average high at each one this month.

Cheapest fares we found from Chicago

Round-trip prices a live search returned in the last two days. They move daily and are not an offer — open a destination to search your own dates.

Atlanta, United States

Atlanta

United States

$67 rt · CHI

Denver, United States

Denver

United States

$89 rt · CHI

Las Vegas, United States

Las Vegas

United States

$116 rt · CHI

Miami, United States

Miami

United States

$139 rt · CHI

Orlando, United States

Orlando

United States

$145 rt · CHI

Dallas, United States

Dallas

United States

$145 rt · CHI

New York, United States

New York

United States

$146 rt · CHI

Guadalajara, Mexico

Guadalajara

Mexico

$158 rt · CHI

Puerto Rico, Puerto Rico

Puerto Rico

Puerto Rico

$162 rt · CHI

Washington D.C., United States

Washington D.C.

United States

$177 rt · CHI

Nashville, United States

Nashville

United States

$184 rt · CHI

Phoenix, United States

Phoenix

United States

$185 rt · CHI

Warm in October

Where it’s warm from Chicago this month

131 of the destinations we found average above 75°F in October. Phoenix leads at 88°F. Temperatures are measured monthly averages, not forecasts.

Phoenix, United States

Phoenix

United States

$185 rt · CHI

Cairo

Egypt

$437 rt · CHI

Mérida

Mexico

$504 rt · CHI

Mumbai

India

$711 rt · CHI

Dakar

Senegal

$735 rt · CHI

Yogyakarta, Indonesia

Yogyakarta

Indonesia

$1,234 rt · CHI

Dhaka, Bangladesh

Dhaka

Bangladesh

$1,636 rt · CHI

Puerto Rico, Puerto Rico

Puerto Rico

Puerto Rico

$162 rt · CHI

See every warm destination, month by month

Everything else we found from Chicago

New Orleans $202 Minneapolis $209 Mexico City $212 Los Angeles $215 San Francisco $220 Boston $229 Seattle $258 Montréal $261 San Diego $264 Guayaquil $266 Costa Rica $291 Toronto $291 Antigua Guatemala $293 Lake Atitlán $293 Quebec City $322 Cancún $329 Tulum $329 Playa del Carmen $329 Calgary $347 Kraków $352 Savannah $365 Key West $371 Punta Cana $373 Guanajuato $375 Montego Bay $380 Aruba $397 Portland $398 Oaxaca $433 Cairo $437 Panama City $440 Barcelona $442 Girona $442 Lloret de Mar $442 Salou $442 Sitges $442 Andorra la Vella $442 Zurich $443 Luzern $443 Cartagena $445 Vancouver $453 Curaçao $457 Skopje $461 Lima $471 Manila $485 Cali $491 Reykjanes $501 Copenhagen $501 Reykjavík $501 Stockholm $504 Mérida $504 Paris $509 Reims $509 Poznań $511 Belgrade $519 Medellín $526 London $528 Quito $541 Rome $542 Civita di Bagnoregio $542 Charleston $542 Rio de Janeiro $550 Haag $550 Utrecht $550 Amsterdam $550 Bangkok $552 Bahamas $556 Dubai $556 Honolulu $560 Madrid $574 Oslo $576 Bogotá $585 Ottawa $595 Warsaw $595 Jamaica $610 Tokyo $612 Gothenburg $615 Vienna $630 Kathmandu $631 Barranquilla $634 Belize $635 Mombasa $666 Diani Beach $666 Budapest $669 Trinidad $670 Tallinn $680 Vilnius $688 Annecy $695 Geneva $695 Bratislava $697 Karachi $701 Fes $702 Varna $702 Mumbai $711 Zagreb $714 Nice $715 Côte d'Azur $715 Saint-Tropez $715 Monaco $715 Èze $715 Prague $715 Malta $716 Valletta $716 Mdina $716 Dar es Salaam $719 Dublin $720 Athens $721 Hydra $721 Spetses $721 Nafplio $721 Delphi $721 Barbados $722 Frigiliana $729 Costa del Sol $729 Torremolinos $729 Nerja $729 Ronda $729 Málaga $729 Marbella $729 Istanbul $730 Cayman Islands $733 Bari $733 Matera $733 Alberobello $733 Ostuni $733 Sarajevo $734 Brygge $734 Brussels $734 Dakar $735 Venice $738 Cusco $744 Machu Picchu $744 Havana $746 Lyon $747 Stuttgart $758 Hanover $759 Alicante $761 Torrevieja $761 Benidorm $761 Zadar $761 Riyadh $764 U.S. Virgin Islands $783 Sofia $784 Amalfi $785 Positano $785 Capri $785 Naples $785 Edinburgh $785 Milan $786 Lake Como $786 Sintra $786 Nazaré $786 Óbidos $786 Comporta $786 Évora $786 Monsanto $786 Lisbon $786 Frankfurt $791 Grenada $795 Marseille $795 Provence $795 Les Baux-de-Provence $795 Gordes $795 Moustiers-Sainte-Marie $795 Yerevan $796 Salvador $796 Casablanca $799 Corfu $799 Bilbao $800 Munich $802 Vlorë $802 Berat $802 Shkodër $802 Tirana $802 Gjirokastra $802 Augsburg $802 Sarandë $802 Sharm El Sheikh $803 Vientiane $803 Sint Maarten $807 Lagos $809 Cyprus $817 Nicosia $817 Ayia Napa $817 Protaras $817 Limassol $817 Marrakech $818 Essaouira $818 Dadès Gorge $818 Toubkal $818 Pristina $819 Doha $820 Ibiza $821 Berlin $822 Manchester $826 Toulouse $832 Turks & Caicos $833 Palma $841 Valldemossa $841 Nairobi $844 Jeddah $850 Tashkent $855 Hanoi $860 Palermo $861 Cologne $861 Bali $867 Ubud $867 Seminyak $867 Helsinki $869 Seville $870 Katowice $879 Samarkand $884 Koh Tao $886 Koh Phangan $886 Koh Samui $886 Bordeaux $887 Tartu $888 Kuala Lumpur $907 Cameron Highlands $907 Glasgow $910 Almaty $910 Gran Canaria $910 Riga $911 Sigulda $911 Tenerife $911 La Gomera $911 Bucharest $913 Bremen $914 Liverpool $920 Podgorica $921 Ulcinj $921 Mykonos $931 Birmingham $931 Phuket $936 São Paulo $938 Singapore $938 Strasbourg $938 Innsbruck $945 Bodrum $945 Ho Chi Minh City $950 Mui Ne $950 Accra $951 Santiago $952 Harare $956 Olympos $958 Kaş $958 Antalya $958 Side $958 Tbilisi $969 Shanghai $972 Guangzhou $974 Beijing $974 Kotor $975 Budva $975 Tivat $975 Herceg Novi $975 Bergen $981 Lahore $986 Agadir $986 Maldives $995 Split $1001 Hvar $1001 Makarska $1001 Brač $1001 Šibenik $1001 Vis $1001 Omiš $1001 Trogir $1001 Abidjan $1002 Ljubljana $1003 Hurghada $1005 Chiang Mai $1006 Chefchaouen $1020 Thessaloniki $1022 Meteora $1022 Montevideo $1024 Asunción $1032 Porto $1036 Gdańsk $1043 Da Nang $1045 Hoi An $1045 Rovaniemi $1049 Delhi $1061 Addis Ababa $1070 Curitiba $1078 Plovdiv $1082 Tunis $1086 Dalat $1090 Bukhara $1092 Chengdu $1098 Sydney $1099 Kutaisi $1105 Florence $1110 Tuscany $1110 Abuja $1117 Hamburg $1131 San Pedro de Atacama $1141 Seoul $1143 Florianópolis $1163 York $1182 Leeds $1182 Douala $1194 Kampala $1210 Osaka $1231 Kyoto $1231 Yogyakarta $1234 Taormina $1243 Catania $1243 Sicily $1243 Sucre $1252 Fiji $1275 Cebu $1286 Buenos Aires $1297 Graz $1308 Funchal $1323 Minsk $1325 Seychelles $1328 Valencia $1337 Taipei $1343 Zanzibar $1344 Stone Town $1344 Victoria Falls $1371 Marmaris $1405 Dalaman $1405 Fethiye $1405 Alanya $1406 Suva $1421 Düsseldorf $1439 Fortaleza $1614 Dhaka $1636 Mauritius $1691 Cape Town $1696 Lusaka $1726 Réunion $1762 Colombo $1767 Kigali $1799 Perth $1860 Goa $1906 Antananarivo $1924 Pattaya $2931 Melbourne $3738

Flying from somewhere else?

Cheap flights from Atlanta Cheap flights from Dallas Cheap flights from Houston Cheap flights from Minneapolis Cheap flights from Denver Cheap flights from Detroit

Good to know

Flying from Chicago — your questions answered

What is the cheapest place to fly from Chicago right now?: Of the fares we found leaving Chicago, the cheapest are Atlanta at $67, Denver at $89, Las Vegas at $116 round trip. These are prices a live search returned in the last couple of days, not a standing offer — availability and price move daily.
Where is it warm right now if I fly from Chicago?: Phoenix is the warmest destination we have a Chicago fare for this month at 88°F. 131 of the destinations we found are above 75°F in October.
Is this every route from Chicago?: No. This page shows the 352 destinations a live fare search returned for Chicago in the last two days, ranked by price. Airlines fly routes we have no current fare for, and thin routes often return nothing at all. Treat it as a snapshot of what was cheap, not a timetable.
When should I book a flight from Chicago?: Six to eight weeks ahead for domestic and short-haul, two to three months for long-haul or peak season. Midweek departures are consistently cheaper than Friday or Sunday, and shifting your dates by a day or two usually saves more than switching airline.