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185 places from Chicago with a recent return price. Prices we can stand behind come first, then the cheapest.
From $247 round trip
37.9% below the middle price here: the cheapest return fare on each of 10 departure dates is usually $323 to $440.
This price is for these exact dates; other dates may cost more.
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| City | From | Dates | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| Fort Lauderdale FLL | $186 | 11 Dec – 21 Dec · 10 nights | ORD → FLL | out 1 stop, back nonstop | found yesterday | See prices for these dates |
| San Juan SJU | $196 | 5 Dec – 12 Dec · 7 nights | MDW → SJU | out 1 stop, back 1 stop | found today | See prices for these dates |
| Detroit DTT | $236 | 8 Dec – 9 Dec · 1 night | ORD → DTW | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
| Fort Myers FMY | $247 | 3 Dec – 3 Dec | ORD → RSW | out nonstop, back nonstop | found yesterday | See prices for these dates |
| Miami MIA | $251 | 21 Dec – 21 Dec | ORD → MIA | out 1 stop, back nonstop | found yesterday | See prices for these dates |
| New York NYC | $284 | 3 Dec – 6 Dec · 3 nights | MDW → EWR | out 1 stop, back 1 stop | found 17 hours ago | See prices for these dates |
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
| Omaha OMA | $350 | 9 Dec – 3 Jan 2027 · 25 nights | ORD → OMA | out 1 stop, back nonstop | found yesterday | See prices for these dates |
| Punta Cana PUJ | $442 | 13 Dec – 20 Dec · 7 nights | ORD → PUJ | out 1 stop, back nonstop | found yesterday | See prices for these dates |
| Mexico City MEX | $737 | 17 Dec – 5 Jan 2027 · 19 nights | MDW → MEX | out 2 stops, back 2 stops | found today | See prices for these dates |
| Abu Dhabi AUH | $776 | 29 Dec – 20 Jan 2027 · 22 nights | ORD → AUH | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
| Sofia SOF | $787 | 20 Dec – 10 Jan 2027 · 21 nights | ORD → SOF | out 2 stops, back 2 stops | found today | See prices for these dates |
| Leon/Guanajuato BJX | $824 | 19 Dec – 2 Jan 2027 · 14 nights | ORD → BJX | out 2 stops, back 2 stops | found yesterday | See prices for these dates |
| Dubai DXB | $888 | 29 Dec – 11 Jan 2027 · 13 nights | ORD → DXB | out 2 stops, back 1 stop | found today | See prices for these dates |
| Buffalo BUF | $893 | 19 Dec – 29 Dec · 10 nights | RFD → BUF | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
| Istanbul IST | $899 | 8 Dec – 8 Jan 2027 · 31 nights | ORD → IST | out 1 stop, back 1 stop | found today | See prices for these dates |
| Belgrade BEG | $1,035 | 23 Dec – 13 Jan 2027 · 21 nights | ORD → BEG | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
| Bishkek BSZ | $1,145 | 26 Dec – 27 Jan 2027 · 32 nights | ORD → BSZ | out 1 stop, back 1 stop | found today | See prices for these dates |
| Catania CTA | $1,347 | 21 Dec – 4 Jan 2027 · 14 nights | ORD → CTA | out 3 stops, back 3 stops | found today | See prices for these dates |
| Moscow MOW | $1,401 | 16 Dec – 13 Jan 2027 · 28 nights | ORD → VKO | out 3 stops, back 3 stops | found 19 hours ago | See prices for these dates |
| Kinshasa FIH | $1,407 | 1 Dec – 22 Dec · 21 nights | ORD → FIH | out 2 stops, back 1 stop | found yesterday | See prices for these dates |
| Tashkent TAS | $1,444 | 14 Dec – 28 Dec · 14 nights | ORD → TAS | out 3 stops, back 3 stops | found 8 hours ago | See prices for these dates |
| Manila MNL | $1,473 | 29 Dec – 16 Jan 2027 · 18 nights | MDW → MNL | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
| Almaty ALA | $1,477 | 16 Dec – 9 Jan 2027 · 24 nights | ORD → ALA | out 3 stops, back 4 stops | found today | See prices for these dates |
| Tbilisi TBS | $1,567 | 21 Dec – 12 Jan 2027 · 22 nights | ORD → TBS | out 3 stops, back 2 stops | found yesterday | See prices for these dates |
| Kigali KGL | $1,726 | 24 Dec – 11 Jan 2027 · 18 nights | ORD → KGL | out 1 stop, back 1 stop | found today | See prices for these dates |
| Saint Martin SFG | $1,917 | 19 Dec – 3 Jan 2027 · 15 nights | ORD → SFG | out 3 stops, back 2 stops | found today | See prices for these dates |
| Dallas DFW | $223 | 30 Dec – 2 Jan 2027 · 3 nights | MDW → DFW | out nonstop, back nonstop | found 3 days ago | See prices for these dates |
| Montreal YMQ | $261 | 12 Dec – 18 Dec · 6 nights | ORD → YUL | out nonstop, back nonstop | found 3 days ago | See prices for these dates |
| Norfolk ORF | $459 | 26 Dec – 30 Dec · 4 nights | ORD → ORF | out nonstop, back 1 stop | found 3 days ago | See prices for these dates |
| Montego Bay MBJ | $529 | 7 Dec – 29 Dec · 22 nights | ORD → MBJ | out nonstop, back nonstop | found 3 days ago | See prices for these dates |
| Freeport FPO | $579 | 19 Dec – 24 Dec · 5 nights | ORD → FPO | out 2 stops, back 1 stop | found 3 days ago | See prices for these dates |
| Warsaw WAW | $687 | 28 Dec – 14 Jan 2027 · 17 nights | ORD → WAW | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| Rome ROM | $710 | 30 Dec – 11 Jan 2027 · 12 nights | ORD → FCO | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
| Glasgow GLA | $817 | 25 Dec – 6 Jan 2027 · 12 nights | ORD → GLA | out 1 stop, back 3 stops | found 3 days ago | See prices for these dates |
| Santo Domingo SDQ | $838 | 23 Dec – 31 Dec · 8 nights | ORD → SDQ | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Lima LIM | $984 | 20 Dec – 8 Jan 2027 · 19 nights | ORD → LIM | out 3 stops, back 1 stop | found 2 days ago | See prices for these dates |
| Denpasar (Bali) DPS | $1,076 | 9 Dec – 22 Dec · 13 nights | ORD → DPS | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| Barcelona BCN | $1,115 | 17 Dec – 11 Jan 2027 · 25 nights | ORD → BCN | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| Hamburg HAM | $1,239 | 19 Dec – 28 Dec · 9 nights | ORD → HAM | out 3 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Manchester MAN | $1,333 | 4 Dec – 14 Dec · 10 nights | MDW → MAN | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Guangzhou CAN | $1,335 | 26 Dec – 8 Jan 2027 · 13 nights | ORD → CAN | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| Doha DOH | $1,434 | 21 Dec – 20 Jan 2027 · 30 nights | ORD → DOH | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| Yekaterinburg SVX | $1,452 | 12 Dec – 11 Jan 2027 · 30 nights | ORD → SVX | out 3 stops, back 3 stops | found 3 days ago | See prices for these dates |
| Palermo PMO | $1,686 | 17 Dec – 3 Jan 2027 · 17 nights | ORD → PMO | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Ulaanbaatar UBN | $1,710 | 16 Dec – 25 Dec · 9 nights | ORD → UBN | out 1 stop, back 2 stops | found 2 days ago | See prices for these dates |
| Baku BAK | $1,717 | 19 Dec – 12 Jan 2027 · 24 nights | ORD → GYD | out 3 stops, back 3 stops | found 3 days ago | See prices for these dates |
| Phuket HKT | $1,822 | 9 Dec – 5 Jan 2027 · 27 nights | ORD → HKT | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
| Krasnodar KRR | $1,914 | 27 Dec – 16 Jan 2027 · 20 nights | ORD → KRR | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| Lahore LHE | $1,959 | 15 Dec – 29 Jan 2027 · 45 nights | ORD → LHE | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
| Atlanta ATL | $145 | 1 Dec – 17 Dec · 16 nights | ORD → ATL | out nonstop, back nonstop | found 6 days ago | See prices for these dates |
| Tampa TPA | $152 | 2 Dec – 16 Dec · 14 nights | ORD → TPA | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| Las Vegas LAS | $179 | 5 Dec – 7 Dec · 2 nights | ORD → LAS | out nonstop, back nonstop | found 4 days ago | See prices for these dates |
| Houston HOU | $181 | 18 Dec – 19 Jan 2027 · 32 nights | ORD → IAH | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Denver DEN | $189 | 13 Dec – 10 Jan 2027 · 28 nights | ORD → DEN | out nonstop, back nonstop | found 6 days ago | See prices for these dates |
| Orlando ORL | $202 | 11 Dec – 13 Dec · 2 nights | MDW → MCO | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| Los Angeles LAX | $215 | 18 Dec – 5 Jan 2027 · 18 nights | ORD → LAX | out nonstop, back nonstop | found 7 days ago | See prices for these dates |
| Raleigh RDU | $246 | 29 Dec – 4 Jan 2027 · 6 nights | ORD → RDU | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| New Orleans MSY | $257 | 30 Dec – 1 Jan 2027 · 2 nights | ORD → MSY | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| San Jose SJO | $291 | 24 Dec – 4 Jan 2027 · 11 nights | ORD → SJO | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Myrtle Beach MYR | $346 | 1 Dec – 3 Dec · 2 nights | ORD → MYR | out 2 stops, back 1 stop | found 4 days ago | See prices for these dates |
| Cancun CUN | $455 | 11 Dec – 26 Dec · 15 nights | ORD → CUN | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| Reykjavik REK | $501 | 31 Dec – 23 Jan 2027 · 23 nights | ORD → KEF | out nonstop, back nonstop | found 5 days ago | See prices for these dates |
| Anchorage ANC | $535 | 7 Dec – 15 Dec · 8 nights | ORD → ANC | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Cartagena CTG | $541 | 14 Dec – 19 Dec · 5 nights | ORD → CTG | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| Nassau NAS | $601 | 1 Dec – 31 Dec · 30 nights | ORD → NAS | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Paris PAR | $613 | 1 Dec – 9 Dec · 8 nights | ORD → CDG | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| Cairo CAI | $690 | 3 Dec – 13 Dec · 10 nights | ORD → CAI | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Honolulu HNL | $699 | 7 Dec – 27 Dec · 20 nights | ORD → HNL | out nonstop, back 1 stop | found 5 days ago | See prices for these dates |
| Barranquilla BAQ | $709 | 14 Dec – 19 Dec · 5 nights | MDW → BAQ | out 2 stops, back 2 stops | found 5 days ago | See prices for these dates |
| Madrid MAD | $787 | 14 Dec – 18 Jan 2027 · 35 nights | ORD → MAD | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Samarkand SKD | $920 | 9 Dec – 29 Jan 2027 · 51 nights | ORD → SKD | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| Larnaca LCA | $949 | 15 Dec – 15 Jan 2027 · 31 nights | ORD → LCA | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| Medina MED | $983 | 1 Dec – 10 Dec · 9 nights | ORD → MED | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| Casablanca CMN | $986 | 31 Dec – 11 Jan 2027 · 11 nights | ORD → CMN | out 2 stops, back 2 stops | found 5 days ago | See prices for these dates |
| London LON | $1,026 | 1 Dec – 8 Dec · 7 nights | MDW → LHR | out 3 stops, back 2 stops | found 5 days ago | See prices for these dates |
| Morelia MLM | $1,028 | 16 Dec – 11 Jan 2027 · 26 nights | MDW → MLM | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |
| Astana NQZ | $1,036 | 6 Dec – 11 Dec · 5 nights | ORD → NQZ | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| Kuala Lumpur KUL | $1,092 | 10 Dec – 18 Dec · 8 nights | ORD → KUL | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| Leeds LBA | $1,182 | 18 Dec – 28 Dec · 10 nights | ORD → LBA | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Chennai MAA | $1,244 | 25 Dec – 20 Jan 2027 · 26 nights | ORD → MAA | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |
| Bangkok BKK | $1,283 | 25 Dec – 10 Jan 2027 · 16 nights | ORD → BKK | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| Novosibirsk OVB | $1,343 | 3 Dec – 7 Dec · 4 nights | ORD → OVB | out 4 stops, back 3 stops | found 4 days ago | See prices for these dates |
| Suva SUV | $1,421 | 1 Dec – 5 Dec · 4 nights | ORD → SUV | out 3 stops, back 3 stops | found 5 days ago | See prices for these dates |
| Perm PEE | $1,430 | 3 Dec – 11 Jan 2027 · 39 nights | ORD → PEE | out 4 stops, back 3 stops | found 6 days ago | See prices for these dates |
| Fortaleza FOR | $1,614 | 19 Dec – 16 Jan 2027 · 28 nights | ORD → FOR | out 3 stops, back 2 stops | found 6 days ago | See prices for these dates |
| Nairobi NBO | $1,626 | 5 Dec – 6 Jan 2027 · 32 nights | ORD → NBO | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Mahe SEZ | $1,628 | 29 Dec – 7 Jan 2027 · 9 nights | ORD → SEZ | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| Minsk MSQ | $1,757 | 10 Dec – 20 Dec · 10 nights | ORD → MSQ | out 3 stops, back 3 stops | found 5 days ago | See prices for these dates |
| Monrovia MLW | $1,858 | 17 Dec – 6 Jan 2027 · 20 nights | ORD → ROB | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |
| Mineralnye Vody MRV | $1,955 | 20 Dec – 28 Dec · 8 nights | ORD → MRV | out 3 stops, back 3 stops | found 6 days ago | See prices for these dates |
| Conakry CKY | $2,092 | 12 Dec – 2 Jan 2027 · 21 nights | ORD → CKY | out 3 stops, back 3 stops | found 5 days ago | See prices for these dates |
| Taipei TPE | $2,566 | 20 Dec – 1 Jan 2027 · 12 nights | MDW → TPE | out 3 stops, back 3 stops | found 5 days ago | See prices for these dates |
| Tokyo TYO | $2,748 | 25 Dec – 10 Jan 2027 · 16 nights | MDW → NRT | out 3 stops, back 3 stops | found 5 days ago | See prices for these dates |