Live City Snapshot
Cheap Flights From Chicago
We track prices to 320 destinations from ORD, MDW airports daily. Here are the best fares right now.
Recent Deals From Chicago
ORD → Bali$832
Found Oct 18 · See the deal →
ORD → Orlando$170
Found Oct 17 · See the deal →
ORD → Fort Lauderdale$133
Found Oct 17 · See the deal →
MDW → Grand Cayman$572
Found Oct 17 · See the deal →
ORD → Grand Cayman$378
Found Oct 16 · See the deal →
ORD → Aruba$452
Found Oct 15 · See the deal →
ORD → San Juan$173
Found Oct 15 · See the deal →
MDW → Barbados$650
Found Oct 14 · See the deal →
ORD → Atlanta$68
Found Oct 10 · See the deal →
MDW → Atlanta$54
Found Oct 7 · 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
| Destination | Deals From |
|---|---|
| Denver(DEN) | $40 |
| Atlanta(ATL) | $54 |
| Fort Lauderdale(FLL) | $66 |
| Tampa(TPA) | $90 |
| Las Vegas(LAS) | $94 |
| Minneapolis(MSP) | $97 |
| Cleveland(CLE) | $97 |
| Dallas/Fort Worth(DFW) | $102 |
| Philadelphia(PHL) | $108 |
| Los Angeles(LAX) | $115 |
| Saint Louis(STL) | $117 |
| Orlando(MCO) | $118 |
| Pittsburgh(PIT) | $137 |
| Indianapolis(IND) | $157 |
| Columbus(CMH) | $157 |
| Miami(MIA) | $171 |
| San Juan(SJU) | $173 |
| Houston Intercontinental(IAH) | $175 |
| Newark(EWR) | $177 |
| Washington Dc - Dulles(IAD) | $177 |
| San Francisco(SFO) | $178 |
| Baltimore(BWI) | $181 |
| Milwaukee(MKE) | $184 |
| Boston(BOS) | $186 |
| Washington Dc(DCA) | $191 |
| New York(JFK) | $197 |
| Houston(HOU) | $209 |
| Grand Rapids(GRR) | $210 |
| Memphis(MEM) | $212 |
| Detroit(DTW) | $217 |
| New York LaGuardia(LGA) | $217 |
| New Orleans(MSY) | $225 |
| Jacksonville(JAX) | $228 |
| Charlotte(CLT) | $228 |
| Toronto(YYZ) | $230 |
| Nashville(BNA) | $230 |
| Raleigh/Durham(RDU) | $230 |
| Hartford(BDL) | $238 |
| Dayton(DAY) | $239 |
| Buffalo(BUF) | $240 |
| Des Moines(DSM) | $244 |
| Dallas Love Field(DAL) | $245 |
| Kansas City(MCI) | $245 |
| Phoenix(PHX) | $250 |
| Santa Barbara(SBA) | $251 |
| Cincinnati(CVG) | $252 |
| Colorado Springs(COS) | $253 |
| Austin(AUS) | $255 |
| Omaha(OMA) | $255 |
| Tulsa(TUL) | $256 |
| Norfolk(ORF) | $256 |
Browse Destinations by Region
| Destination | Deals From |
|---|---|
| San Juan(SJU) | $173 |
| Mexico City(MEX) | $271 |
| Cancun(CUN) | $272 |
| Monterrey(MTY) | $281 |
| Guadalajara(GDL) | $290 |
| Liberia(LIR) | $320 |
| Queretaro(QRO) | $324 |
| Acapulco(ACA) | $341 |
| Montego Bay(MBJ) | $372 |
| Nassau(NAS) | $373 |
| Puerto Vallarta(PVR) | $380 |
| Punta Cana(PUJ) | $385 |
| San Jose Del Cabo(SJD) | $388 |
| Huatulco(HUX) | $398 |
| San Luis Potosi(SLP) | $411 |
| Guanajuato(BJX) | $435 |
| Aruba(AUA) | $452 |
| Aguascalientes(AGU) | $458 |
| Barbados(BGI) | $462 |
| San Salvador(SAL) | $462 |
| Santo Domingo(SDQ) | $468 |
| San Jose(SJO) | $470 |
| Kingston(KIN) | $499 |
| Havana(HAV) | $513 |
| Port Of Spain(POS) | $554 |
| Grand Cayman(GCM) | $572 |
| Guatemala City(GUA) | $573 |
| Bonaire(BON) | $594 |
| Curacao(CUR) | $599 |
| Zihuatanejo/Ixtapa(ZIH) | $609 |
| St. Lucia(UVF) | $617 |
| Tijuana(TIJ) | $621 |
| Grenada(GND) | $628 |
| Panama City(PTY) | $706 |
| Cozumel(CZM) | $712 |
| Destination | Deals From |
|---|---|
| Cartagena(CTG) | $364 |
| Bogota(BOG) | $370 |
| Medellin(MDE) | $430 |
| Cali(CLO) | $441 |
| Quito(UIO) | $454 |
| Guayaquil(GYE) | $507 |
| Rio De Janeiro(GIG) | $507 |
| Santa Cruz(VVI) | $581 |
| Lima(LIM) | $621 |
| Santiago(SCL) | $692 |
| Brasilia(BSB) | $712 |
| Sao Paulo(GRU) | $760 |
| Manaus(MAO) | $771 |
| Porto Alegre(POA) | $802 |
| Cusco(CUZ) | $804 |
| Salvadore(SSA) | $855 |
| Curitiba(CWB) | $860 |
| Recife(REC) | $881 |
| Goiania(GYN) | $885 |
| Buenos Aires(EZE) | $930 |
| Montevideo(MVD) | $973 |
| Asuncion(ASU) | $1,023 |
| Cordoba(COR) | $1,094 |
| Fortaleza(FOR) | $1,396 |
| Destination | Deals From |
|---|---|
| Santa Barbara(SBA) | $251 |
| Burlington(BTV) | $279 |
| Greensboro(GSO) | $284 |
| Rochester(ROC) | $295 |
| Columbia(CAE) | $299 |
| Palm Springs(PSP) | $310 |
| Portland(PWM) | $323 |
| Manchester(MHT) | $372 |
| Maui(OGG) | $396 |
| Lihue(LIH) | $424 |
| Oslo(OSL) | $428 |
| Amsterdam(AMS) | $440 |
| Barcelona(BCN) | $449 |
| Paris(CDG) | $469 |
| Copenhagen(CPH) | $481 |
| Helsinki(HEL) | $534 |
| Honolulu(HNL) | $550 |
| Stockholm(ARN) | $551 |
| Capri(NAP) | $560 |
| Kona(KOA) | $584 |
| Sevilla(SVQ) | $598 |
| Malaga(AGP) | $632 |
| London(LHR) | $638 |
| Vienna(VIE) | $649 |
| Belgrade(BEG) | $649 |
| Venice(VCE) | $649 |
| Zagreb(ZAG) | $649 |
| Frankfurt(FRA) | $658 |
| Prague(PRG) | $661 |
| Dublin(DUB) | $661 |
| Warsaw(WAW) | $675 |
| Madrid(MAD) | $684 |
| Milan(MXP) | $686 |
| Thessaloniki(SKG) | $690 |
| Athens(ATH) | $692 |
| Budapest(BUD) | $692 |
| Geneva(GVA) | $696 |
| Brussels(BRU) | $696 |
| Zurich(ZRH) | $697 |
| Rome(FCO) | $698 |
| Hamburg(HAM) | $703 |
| Nice(NCE) | $713 |
| Sofia(SOF) | $714 |
| Munich(MUC) | $719 |
| Bilbao(BIO) | $726 |
| Lisbon(LIS) | $727 |
| Porto(OPO) | $728 |
| Palma Mallorca(PMI) | $732 |
| Valencia(VLC) | $737 |
| Bucharest(OTP) | $760 |
| Marseille(MRS) | $778 |
| Dubrovnik(DBV) | $786 |
| Ljubliana(LJU) | $800 |
| Lyon(LYS) | $810 |
| Dusseldorf(DUS) | $818 |
| Paris Orly(ORY) | $844 |
| Split(SPU) | $852 |
| Istanbul(IST) | $861 |
| Stuttgart(STR) | $874 |
| Toulouse(TLS) | $884 |
| Cologne(CGN) | $896 |
| Heraklian(HER) | $1,084 |
| Ankara(ESB) | $1,084 |
| Rhodes(RHO) | $1,178 |
| Destination | Deals From |
|---|---|
| Bali(DPS) | $782 |
| Bangkok(BKK) | $830 |
| Delhi(DEL) | $833 |
| Tokyo(NRT) | $837 |
| Bombay(BOM) | $849 |
| Chennai(MAA) | $850 |
| Bangalore(BLR) | $869 |
| Hyderabad(HYD) | $870 |
| Cochin(COK) | $877 |
| Saigon(SGN) | $881 |
| Manila(MNL) | $889 |
| Karachi(KHI) | $890 |
| Chiang Mai(CNX) | $911 |
| Hong Kong(HKG) | $917 |
| Lahore(LHE) | $921 |
| Jakarta(CGK) | $925 |
| Singapore(SIN) | $925 |
| Guangzhou(CAN) | $938 |
| Auckland(AKL) | $940 |
| Dhaka(DAC) | $946 |
| Cebu(CEB) | $950 |
| Kuala Lumpur(KUL) | $950 |
| Hanoi(HAN) | $951 |
| Ahmedabad(AMD) | $960 |
| Phuket(HKT) | $971 |
| Islamabad(ISB) | $983 |
| Da Nang(DAD) | $984 |
| Taipei(TPE) | $1,002 |
| Calcutta(CCU) | $1,008 |
| Wellington(WLG) | $1,034 |
| Christchurch(CHC) | $1,037 |
| Colombo(CMB) | $1,043 |
| Nadi(NAN) | $1,067 |
| Kaohsiung(KHH) | $1,100 |
| Brisbane(BNE) | $1,119 |
| Beijing(PEK) | $1,127 |
| Okinawa(OKA) | $1,139 |
| Kyoto(KIX) | $1,151 |
| Seoul(ICN) | $1,153 |
| Shanghai(PVG) | $1,156 |
| Thiruvananthapuram(TRV) | $1,183 |
| Vientiane(VTE) | $1,231 |
| Tokyo(HND) | $1,242 |
| Nagoya(NGO) | $1,266 |
| Goa(GOI) | $1,279 |
| Kathmandu(KTM) | $1,287 |
| Sapporo(CTS) | $1,318 |
| Penang(PEN) | $1,381 |
| Sydney(SYD) | $1,414 |
| Tahiti(PPT) | $1,419 |
| Melbourne(MEL) | $1,441 |
| Destination | Deals From |
|---|---|
| Algiers(ALG) | $702 |
| Abu Dhabi(AUH) | $725 |
| Dubai(DXB) | $746 |
| Casablanca(CMN) | $763 |
| Cairo(CAI) | $771 |
| Tel Aviv(TLV) | $799 |
| Dammam(DMM) | $803 |
| Sharjah(SHJ) | $817 |
| Riyadh(RUH) | $818 |
| Beirut(BEY) | $825 |
| Bahrain(BAH) | $829 |
| Amman(AMM) | $849 |
| Doha(DOH) | $864 |
| Nairobi(NBO) | $881 |
| Tunis(TUN) | $881 |
| Jeddah(JED) | $882 |
| Kuwait(KWI) | $904 |
| Entebbe(EBB) | $941 |
| Addis Ababa(ADD) | $1,000 |
| Baghdad(BGW) | $1,080 |
| Erbil(EBL) | $1,092 |
| Muscat(MCT) | $1,097 |
| Dar Es Salaam(DAR) | $1,099 |
| Lagos(LOS) | $1,130 |
| Abidjan(ABJ) | $1,132 |
| Damascus(DAM) | $1,148 |
| Accra(ACC) | $1,201 |
| Johannesburg(JNB) | $1,318 |
| Cape Town(CPT) | $1,424 |
Best Months to Fly From Chicago
Jan
$287
Feb
$289
Mar
$346
Apr
$344
May
$243
Jun
$250
Jul
$318
Aug
$238
Sep
$218
Oct
$228
Nov
$275
Dec
$302
Cheapest Average Expensive