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171 places from Chicago with a recent return price. Prices we can stand behind come first, then the cheapest.
From $195 round trip
39.4% below the middle price here: the cheapest return fare on each of 37 departure dates is usually $268 to $345.
This trip has 1 stop.
The map isn't ready yet. Everything is in the list.
| City | From | Dates | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| New York NYC | $195 | 3 Feb 2027 – 9 Feb 2027 · 6 nights | MDW → LGA | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
| Philadelphia PHL | $233 | 15 Dec – 20 Dec · 5 nights | MDW → PHL | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
| Ontario ONT | $246 | 9 Dec – 12 Dec · 3 nights | MDW → ONT | out nonstop, back nonstop | found yesterday | See prices for these dates |
| Las Vegas LAS | $259 | 1 Dec – 9 Dec · 8 nights | MDW → LAS | out 1 stop, back nonstop | found yesterday | See prices for these dates |
| Fort Myers FMY | $349 | 17 Dec – 22 Dec · 5 nights | MDW → RSW | out nonstop, back nonstop | found yesterday | See prices for these dates |
| Seattle SEA | $764 | 15 Nov – 15 Nov | MDW → SEA | out 1 stop, back 1 stop | found yesterday |
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work
| See prices for these dates |
| Havana HAV | $996 | 30 Dec – 10 Jan 2027 · 11 nights | MDW → HAV | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
| Dallas DFW | $168 | 4 Dec – 7 Dec · 3 nights | MDW → DFW | out nonstop, back nonstop | found 3 days ago | See prices for these dates |
| Tampa TPA | $179 | 16 Jan 2027 – 21 Jan 2027 · 5 nights | MDW → TPA | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| Miami MIA | $191 | 12 Dec – 15 Dec · 3 nights | MDW → MIA | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
| Atlanta ATL | $195 | 23 Dec – 27 Dec · 4 nights | MDW → ATL | out nonstop, back nonstop | found 3 days ago | See prices for these dates |
| Denver DEN | $273 | 19 Dec – 22 Dec · 3 nights | MDW → DEN | out nonstop, back nonstop | found 3 days ago | See prices for these dates |
| San Francisco SFO | $300 | 5 Jan 2027 – 13 Jan 2027 · 8 nights | MDW → SFO | out nonstop, back nonstop | found 2 days ago | See prices for these dates |
| Austin AUS | $311 | 22 Dec – 30 Dec · 8 nights | MDW → AUS | out 1 stop, back nonstop | found 2 days ago | See prices for these dates |
| San Diego SAN | $372 | 3 Dec – 11 Dec · 8 nights | MDW → SAN | out nonstop, back nonstop | found 2 days ago | See prices for these dates |
| Morelia MLM | $388 | 30 Jan 2027 – 11 Feb 2027 · 12 nights | MDW → MLM | out nonstop, back nonstop | found 3 days ago | See prices for these dates |
| Oakland OAK | $429 | 14 Apr 2027 – 17 Apr 2027 · 3 nights | MDW → OAK | out nonstop, back nonstop | found 2 days ago | See prices for these dates |
| Cancun CUN | $467 | 20 Jan 2027 – 31 Jan 2027 · 11 nights | MDW → CUN | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| Reno RNO | $472 | 18 May 2027 – 21 May 2027 · 3 nights | MDW → RNO | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
| Edmonton YEA | $572 | 23 Nov – 4 Jan 2027 · 42 nights | MDW → YEG | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
| Nassau NAS | $588 | 22 Dec – 4 Jan 2027 · 13 nights | MDW → NAS | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Toronto YTO | $641 | 30 Dec – 20 Jan 2027 · 21 nights | MDW → YYZ | out 1 stop, back 2 stops | found 3 days ago | See prices for these dates |
| Leon/Guanajuato BJX | $652 | 6 Dec – 13 Dec · 7 nights | MDW → BJX | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Montego Bay MBJ | $677 | 10 Jan 2027 – 15 Jan 2027 · 5 nights | MDW → MBJ | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| Queretaro QRO | $766 | 30 Dec – 9 Jan 2027 · 10 nights | MDW → QRO | out 1 stop, back 2 stops | found 2 days ago | See prices for these dates |
| San Jose del Cabo SJD | $795 | 13 Feb 2027 – 13 Mar 2027 · 28 nights | MDW → SJD | out 2 stops, back 1 stop | found 3 days ago | See prices for these dates |
| Punta Cana PUJ | $801 | 22 Dec – 31 Dec · 9 nights | MDW → PUJ | out 3 stops, back 3 stops | found 3 days ago | See prices for these dates |
| Manila MNL | $836 | 15 Feb 2027 – 1 Mar 2027 · 14 nights | MDW → MNL | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| San Jose SJO | $843 | 5 Jan 2027 – 11 Jan 2027 · 6 nights | MDW → SJO | out 2 stops, back 2 stops | found 3 days ago | See prices for these dates |
| Medellin MDE | $914 | 23 Dec – 4 Jan 2027 · 12 nights | MDW → MDE | out 2 stops, back 3 stops | found 3 days ago | See prices for these dates |
| Istanbul IST | $956 | 19 Jan 2027 – 27 Jan 2027 · 8 nights | MDW → SAW | out 2 stops, back 2 stops | found 3 days ago | See prices for these dates |
| Manzanillo ZLO | $967 | 23 Nov – 29 Nov · 6 nights | MDW → ZLO | out 2 stops, back 1 stop | found 2 days ago | See prices for these dates |
| London LON | $1,020 | 14 Nov – 21 Nov · 7 nights | MDW → LHR | out 3 stops, back 2 stops | found 3 days ago | See prices for these dates |
| Dipolog DPL | $1,067 | 11 Jan 2027 – 15 Feb 2027 · 35 nights | MDW → DPL | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Puerto Plata POP | $1,083 | 16 Dec – 20 Dec · 4 nights | MDW → POP | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Rio de Janeiro RIO | $1,116 | 28 Jan 2027 – 2 Feb 2027 · 5 nights | MDW → GIG | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Papeete PPT | $1,134 | 22 Nov – 4 Dec · 12 nights | MDW → PPT | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| Phuket HKT | $1,322 | 10 Jan 2027 – 24 Jan 2027 · 14 nights | MDW → HKT | out 3 stops, back 3 stops | found 3 days ago | See prices for these dates |
| Warsaw WAW | $1,352 | 2 Dec – 28 Dec · 26 nights | MDW → WAW | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Stockholm STO | $1,452 | 15 Nov – 25 Nov · 10 nights | MDW → ARN | out 2 stops, back 2 stops | found 3 days ago | See prices for these dates |
| Tashkent TAS | $1,459 | 1 Dec – 14 Dec · 13 nights | MDW → TAS | out 3 stops, back 3 stops | found 2 days ago | See prices for these dates |
| Ahmedabad AMD | $1,512 | 10 Jan 2027 – 3 Mar 2027 · 52 nights | MDW → AMD | out 3 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Seoul SEL | $1,610 | 8 Apr 2027 – 25 Apr 2027 · 17 nights | MDW → ICN | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
| Almaty ALA | $1,624 | 25 Dec – 10 Jan 2027 · 16 nights | MDW → ALA | out 3 stops, back 3 stops | found 2 days ago | See prices for these dates |
| Yerevan EVN | $1,807 | 9 Dec – 8 Jan 2027 · 30 nights | MDW → EVN | out 2 stops, back 1 stop | found 3 days ago | See prices for these dates |
| Casablanca CMN | $1,930 | 14 Dec – 4 Jan 2027 · 21 nights | MDW → CMN | out 2 stops, back 2 stops | found 3 days ago | See prices for these dates |
| Osaka OSA | $1,996 | 23 Aug 2027 – 30 Aug 2027 · 7 nights | MDW → ITM | out 3 stops, back 1 stop | found 3 days ago | See prices for these dates |
| Hong Kong HKG | $2,723 | 24 Dec – 10 Jan 2027 · 17 nights | MDW → HKG | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Sydney SYD | $3,030 | 25 Aug 2027 – 3 Sept 2027 · 9 nights | MDW → SYD | out 3 stops, back 1 stop | found 2 days ago | See prices for these dates |
| Bishkek BSZ | $3,201 | 2 Dec – 25 Dec · 23 nights | MDW → BSZ | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Tokyo TYO | $3,629 | 23 Aug 2027 – 30 Aug 2027 · 7 nights | MDW → HND | out 2 stops, back 2 stops | found 3 days ago | See prices for these dates |
| Orlando ORL | $134 | 9 Jan 2027 – 17 Jan 2027 · 8 nights | MDW → MCO | out 1 stop, back nonstop | found 5 days ago | See prices for these dates |
| Fort Lauderdale FLL | $151 | 7 Dec – 10 Dec · 3 nights | MDW → FLL | out 1 stop, back nonstop | found 4 days ago | See prices for these dates |
| Minneapolis MSP | $226 | 13 Jan 2027 – 24 Jan 2027 · 11 nights | MDW → MSP | out nonstop, back 1 stop | found 6 days ago | See prices for these dates |
| Los Angeles LAX | $236 | 9 Dec – 13 Dec · 4 nights | MDW → LAX | out nonstop, back nonstop | found 5 days ago | See prices for these dates |
| Washington WAS | $242 | 1 Jan 2027 – 6 Jan 2027 · 5 nights | MDW → IAD | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| Baltimore BWI | $265 | 1 Jan 2027 – 6 Jan 2027 · 5 nights | MDW → BWI | out nonstop, back 1 stop | found 5 days ago | See prices for these dates |
| Boston BOS | $277 | 21 Nov – 22 Nov · 1 night | MDW → BOS | out nonstop, back nonstop | found 5 days ago | See prices for these dates |
| Charlotte CLT | $286 | 18 Dec – 21 Dec · 3 nights | MDW → CLT | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Houston HOU | $289 | 29 Dec – 2 Jan 2027 · 4 nights | MDW → IAH | out 1 stop, back nonstop | found 7 days ago | See prices for these dates |
| San Juan SJU | $297 | 20 Jan 2027 – 27 Jan 2027 · 7 nights | MDW → SJU | out 2 stops, back 1 stop | found 5 days ago | See prices for these dates |
| Nashville BNA | $298 | 30 Nov – 3 Dec · 3 nights | MDW → BNA | out 1 stop, back nonstop | found 6 days ago | See prices for these dates |
| Cleveland CLE | $306 | 12 Dec – 27 Dec · 15 nights | MDW → CLE | out nonstop, back nonstop | found 4 days ago | See prices for these dates |
| Phoenix PHX | $311 | 18 Dec – 10 Jan 2027 · 23 nights | MDW → PHX | out nonstop, back nonstop | found 4 days ago | See prices for these dates |
| Guadalajara GDL | $346 | 15 Nov – 22 Nov · 7 nights | MDW → GDL | out nonstop, back nonstop | found 4 days ago | See prices for these dates |
| Salt Lake City SLC | $353 | 24 Dec – 30 Dec · 6 nights | MDW → SLC | out nonstop, back nonstop | found 4 days ago | See prices for these dates |
| Mexico City MEX | $368 | 5 Dec – 9 Dec · 4 nights | MDW → MEX | out 1 stop, back nonstop | found 6 days ago | See prices for these dates |
| San Luis Potosi SLP | $392 | 3 Dec – 10 Dec · 7 nights | MDW → SLP | out nonstop, back nonstop | found 4 days ago | See prices for these dates |
| Raleigh RDU | $398 | 25 Nov – 30 Nov · 5 nights | MDW → RDU | out 1 stop, back 2 stops | found 5 days ago | See prices for these dates |
| Indianapolis IND | $495 | 22 Nov – 27 Nov · 5 nights | MDW → IND | out nonstop, back 2 stops | found 4 days ago | See prices for these dates |
| Flint FNT | $512 | 4 Dec – 11 Dec · 7 nights | MDW → FNT | out 2 stops, back 2 stops | found 5 days ago | See prices for these dates |
| Long Beach LGB | $513 | 1 Jul 2027 – 4 Jul 2027 · 3 nights | MDW → LGB | out nonstop, back nonstop | found 5 days ago | See prices for these dates |
| Jacksonville JAX | $532 | 3 Apr 2027 – 10 Apr 2027 · 7 nights | MDW → JAX | out nonstop, back nonstop | found 4 days ago | See prices for these dates |
| Newburgh SWF | $554 | 11 Mar 2027 – 13 Mar 2027 · 2 nights | MDW → SWF | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| Aguascalientes AGU | $616 | 29 Jun 2027 – 20 Jul 2027 · 21 nights | MDW → AGU | out 2 stops, back 1 stop | found 6 days ago | See prices for these dates |
| Honolulu HNL | $651 | 23 Nov – 8 Dec · 15 nights | MDW → HNL | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Sacramento SAC | $705 | 23 Nov – 29 Nov · 6 nights | MDW → SMF | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Dubai DXB | $793 | 9 Feb 2027 – 25 Feb 2027 · 16 nights | MDW → DXB | out 2 stops, back 1 stop | found 5 days ago | See prices for these dates |
| Reykjavik REK | $846 | 15 Mar 2027 – 27 Mar 2027 · 12 nights | MDW → KEF | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| Guatemala City GUA | $865 | 16 Nov – 1 Dec · 15 nights | MDW → GUA | out 2 stops, back 1 stop | found 6 days ago | See prices for these dates |
| Berlin BER | $893 | 1 Feb 2027 – 10 Feb 2027 · 9 nights | MDW → BER | out 2 stops, back 1 stop | found 6 days ago | See prices for these dates |
| Munich MUC | $936 | 1 Feb 2027 – 10 Feb 2027 · 9 nights | MDW → MUC | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |
| Paris PAR | $975 | 8 Jan 2027 – 15 Jan 2027 · 7 nights | MDW → CDG | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Prague PRG | $981 | 3 Feb 2027 – 14 Feb 2027 · 11 nights | MDW → PRG | out 3 stops, back 2 stops | found 5 days ago | See prices for these dates |
| Belgrade BEG | $1,128 | 23 Dec – 27 Jan 2027 · 35 nights | MDW → BEG | out 3 stops, back 2 stops | found 5 days ago | See prices for these dates |
| Rome ROM | $1,153 | 2 Dec – 9 Dec · 7 nights | MDW → FCO | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |
| Zurich ZRH | $1,171 | 25 Dec – 7 Jan 2027 · 13 nights | MDW → ZRH | out 3 stops, back 3 stops | found 6 days ago | See prices for these dates |
| Saint Thomas STT | $1,203 | 20 Nov – 24 Nov · 4 nights | MDW → STT | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| Buenos Aires BUE | $1,217 | 1 Feb 2027 – 4 Mar 2027 · 31 nights | MDW → EZE | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |
| Budapest BUD | $1,248 | 10 Dec – 18 Dec · 8 nights | MDW → BUD | out 3 stops, back 1 stop | found 6 days ago | See prices for these dates |
| Mumbai BOM | $1,260 | 11 Jan 2027 – 10 Feb 2027 · 30 nights | MDW → BOM | out 2 stops, back 2 stops | found 5 days ago | See prices for these dates |
| Vilnius VNO | $1,260 | 19 Dec – 14 Jan 2027 · 26 nights | MDW → VNO | out 3 stops, back 3 stops | found 7 days ago | See prices for these dates |
| Davao City DVO | $1,354 | 18 Jan 2027 – 25 Jan 2027 · 7 nights | MDW → DVO | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |
| Tbilisi TBS | $1,590 | 5 Jan 2027 – 15 Jan 2027 · 10 nights | MDW → TBS | out 2 stops, back 1 stop | found 4 days ago | See prices for these dates |
| Cairo CAI | $1,620 | 14 Dec – 21 Dec · 7 nights | MDW → CAI | out 1 stop, back 2 stops | found 4 days ago | See prices for these dates |
| Karachi KHI | $1,623 | 18 Nov – 30 Nov · 12 nights | MDW → KHI | out 2 stops, back 2 stops | found 4 days ago | See prices for these dates |
| Tagbilaran TAG | $1,625 | 1 Jun 2027 – 9 Jun 2027 · 8 nights | MDW → TAG | out 2 stops, back 2 stops | found 5 days ago | See prices for these dates |
| Agadir AGA | $1,635 | 9 Dec – 25 Dec · 16 nights | MDW → AGA | out 2 stops, back 3 stops | found 5 days ago | See prices for these dates |
| Beijing BJS | $1,674 | 3 Dec – 21 Jan 2027 · 49 nights | MDW → PEK | out 2 stops, back 1 stop | found 6 days ago | See prices for these dates |
| Skopje SKP | $1,687 | 24 Dec – 4 Jan 2027 · 11 nights | MDW → SKP | out 3 stops, back 3 stops | found 6 days ago | See prices for these dates |
| Sanya SYX | $1,706 | 3 Jan 2027 – 17 Jan 2027 · 14 nights | MDW → SYX | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |
| Shanghai SHA | $1,786 | 3 Jan 2027 – 17 Jan 2027 · 14 nights | MDW → PVG | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| Barcelona BCN | $1,789 | 12 Dec – 2 Jan 2027 · 21 nights | MDW → BCN | out 3 stops, back 3 stops | found 5 days ago | See prices for these dates |
| Bangkok BKK | $1,877 | 23 Mar 2027 – 4 Apr 2027 · 12 nights | MDW → BKK | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |
| Male MLE | $1,895 | 10 Jan 2027 – 25 Jan 2027 · 15 nights | MDW → MLE | out 3 stops, back 2 stops | found 7 days ago | See prices for these dates |
| Dushanbe DYU | $2,252 | 5 Jan 2027 – 18 Jan 2027 · 13 nights | MDW → DYU | out 2 stops, back 2 stops | found 7 days ago | See prices for these dates |
| Mahe SEZ | $2,263 | 30 Dec – 13 Jan 2027 · 14 nights | MDW → SEZ | out 2 stops, back 3 stops | found 6 days ago | See prices for these dates |
| Kathmandu KTM | $2,305 | 10 Dec – 23 Dec · 13 nights | MDW → KTM | out 3 stops, back 1 stop | found 6 days ago | See prices for these dates |
| Cebu City CEB | $2,354 | 8 Dec – 5 Jan 2027 · 28 nights | MDW → CEB | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |
| Zanzibar ZNZ | $2,566 | 23 Dec – 5 Jan 2027 · 13 nights | MDW → ZNZ | out 3 stops, back 3 stops | found 7 days ago | See prices for these dates |
| Nairobi NBO | $2,645 | 24 Dec – 4 Jan 2027 · 11 nights | MDW → NBO | out 2 stops, back 1 stop | found 7 days ago | See prices for these dates |
| Mombasa MBA | $2,666 | 28 Dec – 7 Jan 2027 · 10 nights | MDW → MBA | out 3 stops, back 2 stops | found 7 days ago | See prices for these dates |
| Madrid MAD | $2,777 | 20 Dec – 2 Jan 2027 · 13 nights | MDW → MAD | out 2 stops, back 2 stops | found 5 days ago | See prices for these dates |
| Hanoi HAN | $2,853 | 10 Dec – 24 Dec · 14 nights | MDW → HAN | out 2 stops, back 2 stops | found 5 days ago | See prices for these dates |
| Doha DOH | $2,961 | 17 Feb 2027 – 25 Feb 2027 · 8 nights | MDW → DOH | out 2 stops, back 2 stops | found 4 days ago | See prices for these dates |
| Larnaca LCA | $4,500 | 12 Dec – 10 Jan 2027 · 29 nights | MDW → LCA | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |