Live City Snapshot
Cheap Flights From Chicago
We track prices to 336 destinations from ORD, MDW airports daily. Here are the best fares right now.
Recent Deals From Chicago
ORD → Fort Lauderdale$84
Found Nov 8 · See the deal →
MDW → San Juan$205
Found Nov 5 · See the deal →
ORD → Beirut$790
Found Nov 3 · See the deal →
ORD → Kyoto$659
Found Nov 1 · See the deal →
MDW → Medellin$467
Found Oct 29 · See the deal →
ORD → San Juan$207
Found Oct 29 · See the deal →
MDW → Bali$832
Found Oct 27 · See the deal →
MDW → Montreal$297
Found Oct 26 · See the deal →
ORD → Atlanta$60
Found Oct 24 · See the deal →
ORD → Maui$475
Found Oct 22 · See the deal →
Deal Prices to Watch For
When fares from Chicago drop to these prices, they are worth booking. Based on our ongoing price tracking for each route.
Top Destinations
Browse Destinations by Region
| Destination | Deals From |
|---|---|
| San Juan(SJU) | $266 |
| Mexico City(MEX) | $286 |
| Guadalajara(GDL) | $313 |
| Cancun(CUN) | $322 |
| Monterrey(MTY) | $325 |
| Puerto Vallarta(PVR) | $333 |
| San Jose Del Cabo(SJD) | $338 |
| Acapulco(ACA) | $371 |
| Montego Bay(MBJ) | $382 |
| Nassau(NAS) | $398 |
| Punta Cana(PUJ) | $405 |
| Queretaro(QRO) | $421 |
| San Jose, Costa Rica(SJO) | $424 |
| Santo Domingo(SDQ) | $428 |
| Guanajuato(BJX) | $435 |
| Huatulco(HUX) | $446 |
| San Salvador(SAL) | $463 |
| Aguascalientes(AGU) | $473 |
| San Luis Potosi(SLP) | $483 |
| Havana(HAV) | $504 |
| Managua(MGA) | $508 |
| San Pedro Sula(SAP) | $554 |
| Aruba(AUA) | $559 |
| Liberia(LIR) | $568 |
| Guatemala City(GUA) | $577 |
| Grand Cayman(GCM) | $583 |
| Kingston(KIN) | $592 |
| Barbados(BGI) | $612 |
| Bonaire(BON) | $618 |
| Port Of Spain(POS) | $620 |
| Tijuana(TIJ) | $646 |
| St. Lucia(UVF) | $649 |
| Curacao(CUR) | $657 |
| Zihuatanejo/Ixtapa(ZIH) | $662 |
| Belize City(BZE) | $670 |
| Panama City(PTY) | $679 |
| Grenada(GND) | $702 |
| Cozumel(CZM) | $720 |
| Roatan(RTB) | $739 |
| Destination | Deals From |
|---|---|
| Cartagena(CTG) | $370 |
| Bogota(BOG) | $445 |
| Medellin(MDE) | $447 |
| Quito(UIO) | $461 |
| Cali(CLO) | $478 |
| Guayaquil(GYE) | $510 |
| Rio De Janeiro(GIG) | $518 |
| Lima(LIM) | $635 |
| Santa Cruz(VVI) | $700 |
| Santiago(SCL) | $704 |
| Brasilia(BSB) | $738 |
| Sao Paulo(GRU) | $818 |
| Manaus(MAO) | $847 |
| Porto Alegre(POA) | $872 |
| Salvadore(SSA) | $906 |
| Cusco(CUZ) | $909 |
| Curitiba(CWB) | $926 |
| Buenos Aires(EZE) | $927 |
| Recife(REC) | $944 |
| Montevideo(MVD) | $1,023 |
| Goiania(GYN) | $1,061 |
| Asuncion(ASU) | $1,088 |
| Cordoba(COR) | $1,103 |
| Fortaleza(FOR) | $1,153 |
| Destination | Deals From |
|---|---|
| Rochester(ROC) | $277 |
| Burlington(BTV) | $279 |
| Santa Barbara(SBA) | $286 |
| Greensboro(GSO) | $294 |
| Columbia(CAE) | $299 |
| Portland, Maine(PWM) | $308 |
| Palm Springs(PSP) | $310 |
| Bangor(BGR) | $355 |
| Bozeman(BZN) | $359 |
| Manchester(MHT) | $366 |
| Glacier(FCA) | $399 |
| Lihue(LIH) | $424 |
| Flores(FRS) | $476 |
| Stockholm(ARN) | $490 |
| Honolulu(HNL) | $548 |
| Maui(OGG) | $562 |
| Oslo(OSL) | $577 |
| Helsinki(HEL) | $579 |
| Copenhagen(CPH) | $605 |
| Kona(KOA) | $609 |
| Fairbanks(FAI) | $610 |
| Dublin(DUB) | $647 |
| Rome(FCO) | $651 |
| Barcelona(BCN) | $656 |
| Hilo(ITO) | $678 |
| Capri(NAP) | $693 |
| Warsaw(WAW) | $697 |
| Budapest(BUD) | $698 |
| Zurich(ZRH) | $699 |
| Athens(ATH) | $699 |
| Geneva(GVA) | $699 |
| Milan(MXP) | $699 |
| Prague(PRG) | $699 |
| Thessaloniki(SKG) | $699 |
| Sofia(SOF) | $699 |
| Venice(VCE) | $700 |
| Malaga(AGP) | $705 |
| Bucharest(OTP) | $708 |
| Belgrade(BEG) | $708 |
| Madrid(MAD) | $710 |
| Frankfurt(FRA) | $712 |
| Paris(CDG) | $713 |
| Bilbao(BIO) | $723 |
| Valencia(VLC) | $723 |
| Vienna(VIE) | $723 |
| Nice(NCE) | $725 |
| Zagreb(ZAG) | $726 |
| Marseille(MRS) | $728 |
| Hamburg(HAM) | $732 |
| Munich(MUC) | $735 |
| London(LHR) | $735 |
| Berlin(BER) | $739 |
| Sevilla(SVQ) | $743 |
| Porto(OPO) | $751 |
| Lisbon(LIS) | $762 |
| Dusseldorf(DUS) | $766 |
| Lyon(LYS) | $766 |
| Toulouse(TLS) | $768 |
| Palma Mallorca(PMI) | $773 |
| Brussels(BRU) | $793 |
| Paris Orly(ORY) | $793 |
| Istanbul(IST) | $794 |
| Amsterdam(AMS) | $828 |
| Ljubliana(LJU) | $849 |
| Cologne(CGN) | $864 |
| Stuttgart(STR) | $879 |
| Granada, Spain(GRX) | $894 |
| Dubrovnik(DBV) | $896 |
| Split(SPU) | $937 |
| KTI(KTI) | $959 |
| Heraklian(HER) | $982 |
| Ankara(ESB) | $1,003 |
| Izmir(ADB) | $1,063 |
| Rhodes(RHO) | $1,128 |
| Destination | Deals From |
|---|---|
| Manila(MNL) | $894 |
| Bombay(BOM) | $900 |
| Delhi(DEL) | $901 |
| Jakarta(CGK) | $911 |
| Karachi(KHI) | $915 |
| Bangkok(BKK) | $920 |
| Saigon(SGN) | $920 |
| Kuala Lumpur(KUL) | $920 |
| Bali(DPS) | $937 |
| Singapore(SIN) | $939 |
| Cebu(CEB) | $940 |
| Cochin(COK) | $943 |
| Hanoi(HAN) | $951 |
| Hyderabad(HYD) | $952 |
| Phuket(HKT) | $961 |
| Chennai(MAA) | $964 |
| Beijing(PEK) | $966 |
| Bangalore(BLR) | $969 |
| Hong Kong(HKG) | $987 |
| Penang(PEN) | $990 |
| Shanghai(PVG) | $994 |
| Chiang Mai(CNX) | $995 |
| Islamabad(ISB) | $1,000 |
| Lahore(LHE) | $1,006 |
| Da Nang(DAD) | $1,031 |
| Taipei(TPE) | $1,041 |
| Kota Kinabalu(BKI) | $1,044 |
| Dhaka(DAC) | $1,052 |
| Calcutta(CCU) | $1,053 |
| Ahmedabad(AMD) | $1,076 |
| Guangzhou(CAN) | $1,080 |
| Kyoto(KIX) | $1,084 |
| Auckland(AKL) | $1,090 |
| Colombo(CMB) | $1,094 |
| Surabaya(SUB) | $1,100 |
| Kathmandu(KTM) | $1,123 |
| Brisbane(BNE) | $1,157 |
| Shenzhen(SZX) | $1,158 |
| Thiruvananthapuram(TRV) | $1,168 |
| Destination | Deals From |
|---|---|
| Cairo(CAI) | $710 |
| Algiers(ALG) | $753 |
| Dubai(DXB) | $760 |
| Casablanca(CMN) | $763 |
| Abu Dhabi(AUH) | $773 |
| Beirut(BEY) | $822 |
| Riyadh(RUH) | $833 |
| Jeddah(JED) | $869 |
| Dammam(DMM) | $875 |
| Sharjah(SHJ) | $877 |
| Doha(DOH) | $884 |
| Amman(AMM) | $899 |
| Nairobi(NBO) | $925 |
| Kuwait(KWI) | $939 |
| Tunis(TUN) | $955 |
| Lagos(LOS) | $960 |
| Bahrain(BAH) | $976 |
| Tel Aviv(TLV) | $1,061 |
| Baghdad(BGW) | $1,082 |
| Damascus(DAM) | $1,089 |
| Erbil(EBL) | $1,092 |
| Muscat(MCT) | $1,094 |
| Dar Es Salaam(DAR) | $1,096 |
| Addis Ababa(ADD) | $1,100 |
| Entebbe(EBB) | $1,113 |
| Abidjan(ABJ) | $1,146 |
| Cape Town(CPT) | $1,149 |
Best Months to Fly From Chicago
Jan
$205
Feb
$216
Mar
$295
Apr
$289
May
$262
Jun
$262
Jul
$278
Aug
$245
Sep
$227
Oct
$228
Nov
$236
Dec
$226
Cheapest Average Expensive