Departing Chicago

Cheap Flights from Chicago

The cheapest fares we found leaving Chicago right now are Denver at $115, Los Angeles at $126 and Orlando at $145 round trip. Below are 284 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.

Denver, United States

Denver

United States

$115 rt · CHI · seen Aug 18

Los Angeles, United States

Los Angeles

United States

$126 rt · CHI · seen Aug 18

Orlando, United States

Orlando

United States

$145 rt · CHI · seen Aug 20

Las Vegas, United States

Las Vegas

United States

$145 rt · CHI · seen Aug 18

Minneapolis, United States

Minneapolis

United States

$145 rt · CHI · seen Aug 18

New Orleans, United States

New Orleans

United States

$145 rt · CHI · seen Aug 18

Miami, United States

Miami

United States

$158 rt · CHI · seen Aug 18

Washington D.C., United States

Washington D.C.

United States

$159 rt · CHI · seen Aug 20

Nashville, United States

Nashville

United States

$189 rt · CHI · seen Aug 18

Toronto, Canada

Toronto

Canada

$196 rt · CHI · seen Aug 20

New York, United States

New York

United States

$202 rt · CHI · seen Aug 20

San Francisco, United States

San Francisco

United States

$203 rt · CHI · seen Aug 18

Warm in September

Where it’s warm from Chicago this month

165 of the destinations we found average above 75°F in September. Puerto Rico leads at 88°F with the sea at 86°F. Temperatures are measured monthly averages, not forecasts.

Puerto Rico, Puerto Rico

Puerto Rico

Puerto Rico

$273 rt · CHI · seen Aug 20

Montego Bay, Jamaica

Montego Bay

Jamaica

$373 rt · CHI · seen Aug 18

Manila, Philippines

Manila

Philippines

$494 rt · CHI · seen Aug 18

Mombasa

Kenya

$666 rt · CHI · seen Aug 22

Bangkok, Thailand

Bangkok

Thailand

$763 rt · CHI · seen Aug 18

Alanya

Turkey

$781 rt · CHI · seen Aug 21

Dar es Salaam, Tanzania

Dar es Salaam

Tanzania

$789 rt · CHI · seen Aug 25

Cyprus

Cyprus

$838 rt · CHI · seen Aug 21

See every warm destination, month by month

Everything else we found from Chicago

Boston $205 Atlanta $207 Dallas $223 Guadalajara $234 San Diego $241 Phoenix $247 Oslo $261 Honolulu $271 Puerto Rico $273 Mexico City $280 Portland $284 Antigua Guatemala $289 Lake Atitlán $289 Seattle $303 Charleston $310 Montréal $324 Mérida $331 Calgary $343 Key West $351 Cancún $357 Tulum $357 Playa del Carmen $357 Cartagena $367 Bahamas $372 Montego Bay $373 Cairo $378 Milan $388 Lake Como $388 Sint Maarten $398 Madrid $406 Ottawa $406 Punta Cana $409 Rome $410 Civita di Bagnoregio $410 Barranquilla $410 Costa Rica $416 Quebec City $419 Porto $420 Athens $422 Hydra $422 Spetses $422 Nafplio $422 Delphi $422 Bogotá $424 Geneva $425 Annecy $425 Vienna $427 Helsinki $436 Guanajuato $437 Warsaw $438 Reykjavík $442 Reykjanes $442 Belize $446 Jamaica $450 Medellín $464 Pristina $472 Rio de Janeiro $473 Paris $479 Reims $479 Quito $481 Copenhagen $486 Dublin $487 Manila $494 Aruba $500 Turks & Caicos $509 Kraków $513 Düsseldorf $518 Monsanto $520 Amsterdam $520 Haag $520 Utrecht $520 Lisbon $520 Évora $520 Sintra $520 Nazaré $520 Óbidos $520 Comporta $520 Frankfurt $528 Poznań $534 Vancouver $542 Guayaquil $543 Sofia $544 Jeddah $545 Lima $583 Belgrade $591 Stockholm $592 Lagos $596 Istanbul $599 Havana $603 U.S. Virgin Islands $606 Montevideo $627 Karachi $628 Barcelona $630 Girona $630 Lloret de Mar $630 Salou $630 Sitges $630 Andorra la Vella $630 Tashkent $631 London $634 Curaçao $634 Abidjan $642 Budapest $642 Seoul $647 Vilnius $653 Tallinn $660 Mumbai $665 Mombasa $666 Diani Beach $666 Berlin $668 Frigiliana $669 Costa del Sol $669 Torremolinos $669 Nerja $669 Ronda $669 Málaga $669 Marbella $669 Casablanca $676 Dubai $677 Palma $680 Valldemossa $680 Sharm El Sheikh $681 Hamburg $703 Taipei $726 Skopje $733 Singapore $738 Brygge $740 Brussels $740 Munich $746 Augsburg $746 Malta $753 Valletta $753 Mdina $753 Valencia $761 Zadar $761 Zurich $763 Luzern $763 Vientiane $763 Bangkok $763 Bilbao $774 Alanya $781 Lyon $784 Delhi $784 Panama City $789 Dar es Salaam $789 Tokyo $793 Prague $801 Florence $806 Tuscany $806 Doha $812 Riyadh $819 São Paulo $825 Toulouse $832 Cyprus $838 Nicosia $838 Ayia Napa $838 Protaras $838 Limassol $838 Sarandë $847 Tirana $847 Vlorë $847 Berat $847 Shkodër $847 Gjirokastra $847 Alicante $851 Torrevieja $851 Benidorm $851 Santiago $856 Ho Chi Minh City $856 Mui Ne $856 Yerevan $860 Palermo $861 Nairobi $863 Edinburgh $870 Seville $870 Amalfi $876 Positano $876 Capri $876 Naples $876 Tbilisi $879 Kampala $880 Bordeaux $887 Cebu $891 Hanoi $894 Kotor $901 Budva $901 Tivat $901 Herceg Novi $901 Barbados $904 Ibiza $906 Taormina $912 Catania $912 Sicily $912 Bremen $914 Olympos $925 Kaş $925 Antalya $925 Side $925 Kuala Lumpur $930 Cameron Highlands $930 Bali $938 Ubud $938 Seminyak $938 Phuket $943 Innsbruck $945 Sigulda $954 Riga $954 Harare $964 Accra $965 Beijing $967 Hoi An $968 Da Nang $968 Bucharest $969 Shanghai $974 Guangzhou $980 Bergen $981 Lahore $986 Marrakech $989 Essaouira $989 Dadès Gorge $989 Toubkal $989 Samarkand $992 Almaty $994 Ljubljana $1003 Gran Canaria $1018 Kigali $1018 Tenerife $1025 La Gomera $1025 Florianópolis $1031 Tunis $1033 Kutaisi $1058 Addis Ababa $1060 Fes $1072 Curitiba $1078 Buenos Aires $1083 Bukhara $1092 Marmaris $1093 Dalaman $1093 Fethiye $1093 Fortaleza $1097 Chengdu $1098 Bodrum $1113 Colombo $1115 Abuja $1117 Graz $1119 Hurghada $1125 Funchal $1179 Thessaloniki $1188 Meteora $1188 Podgorica $1265 Ulcinj $1265 Pattaya $1267 Chiang Mai $1290 Sydney $1291 Koh Samui $1356 Koh Tao $1356 Koh Phangan $1356 Victoria Falls $1371 Kathmandu $1388 Osaka $1417 Kyoto $1417 Zanzibar $1423 Stone Town $1423 Asunción $1443 Seychelles $1452 Minsk $1455 Venice $1478 Melbourne $1619 Antananarivo $1734 Réunion $1762 Maldives $1958 Cape Town $2053

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 Denver at $115, Los Angeles at $126, Orlando at $145 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?: Puerto Rico is the warmest destination we have a Chicago fare for this month at 88°F, with the sea at 86°F. 165 of the destinations we found are above 75°F in September.
Is this every route from Chicago?: No. This page shows the 284 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.