Cheapest Destinations from Chicago
All Destinations from Chicago
| Destination | Country | Region | Est. Price | Flight Time |
|---|---|---|---|---|
| MTYMonterrey | Mexico | central america-caribbean | $111 | ~4h |
| NASNassau | Bahamas | central america-caribbean | $111 | ~4h |
| CUNCancun | Mexico | central america-caribbean | $122 | ~4h |
| GCMGrand Cayman | Cayman Islands | central america-caribbean | $136 | ~4h |
| MEXMexico City | Mexico | central america-caribbean | $142 | ~4h |
| MBJMontego Bay | Jamaica | central america-caribbean | $145 | ~4h |
| GDLGuadalajara | Mexico | central america-caribbean | $146 | ~4h |
| PVRPuerto Vallarta | Mexico | central america-caribbean | $150 | ~5h |
| KINKingston | Jamaica | central america-caribbean | $150 | ~5h |
| SJDLos Cabos | Mexico | central america-caribbean | $152 | ~5h |
| SDQSanto Domingo | Dominican Republic | central america-caribbean | $164 | ~5h |
| PUJPunta Cana | Dominican Republic | central america-caribbean | $167 | ~5h |
| SJUSan Juan | Puerto Rico | central america-caribbean | $174 | ~5h |
| STTSt. Thomas | US Virgin Islands | central america-caribbean | $178 | ~5h |
| SXMSt. Maarten | Sint Maarten | central america-caribbean | $185 | ~5h |
| AUAAruba | Aruba | central america-caribbean | $194 | ~6h |
| ANUAntigua | Antigua and Barbuda | central america-caribbean | $194 | ~6h |
| CURCuracao | Curacao | central america-caribbean | $198 | ~6h |
| UVFSt. Lucia | Saint Lucia | central america-caribbean | $213 | ~6h |
| BGIBarbados | Barbados | central america-caribbean | $221 | ~6h |
| POSTrinidad | Trinidad and Tobago | central america-caribbean | $227 | ~6h |
| KEFReykjavik | Iceland | europe | $247 | ~7h |
| DUBDublin | Ireland | europe | $308 | ~8h |
| GLAGlasgow | United Kingdom | europe | $308 | ~8h |
| EDIEdinburgh | United Kingdom | europe | $311 | ~8h |
| MANManchester | United Kingdom | europe | $321 | ~9h |
| BHXBirmingham | United Kingdom | europe | $325 | ~9h |
| OPOPorto | Portugal | europe | $331 | ~9h |
| LHRLondon | United Kingdom | europe | $332 | ~9h |
| LISLisbon | Portugal | europe | $336 | ~9h |
| OSLOslo | Norway | europe | $339 | ~9h |
| AMSAmsterdam | Netherlands | europe | $345 | ~9h |
| FAOFaro | Portugal | europe | $346 | ~9h |
| CDGParis | France | europe | $348 | ~9h |
| BRUBrussels | Belgium | europe | $349 | ~9h |
| MADMadrid | Spain | europe | $352 | ~9h |
| SVQSeville | Spain | europe | $353 | ~9h |
| DUSDusseldorf | Germany | europe | $354 | ~9h |
| HAMHamburg | Germany | europe | $357 | ~9h |
| CPHCopenhagen | Denmark | europe | $358 | ~10h |
| ARNStockholm | Sweden | europe | $358 | ~10h |
| AGPMalaga | Spain | europe | $361 | ~10h |
| FRAFrankfurt | Germany | europe | $364 | ~10h |
| LYSLyon | France | europe | $367 | ~10h |
| GVAGeneva | Switzerland | europe | $369 | ~10h |
| BCNBarcelona | Spain | europe | $371 | ~10h |
| BERBerlin | Germany | europe | $371 | ~10h |
| ZRHZurich | Switzerland | europe | $372 | ~10h |
| HELHelsinki | Finland | europe | $372 | ~10h |
| MRSMarseille | France | europe | $375 | ~10h |
| TLLTallinn | Estonia | europe | $375 | ~10h |
| IBZIbiza | Spain | europe | $376 | ~10h |
| MXPMilan | Italy | europe | $379 | ~10h |
| PMIPalma de Mallorca | Spain | europe | $379 | ~10h |
| MUCMunich | Germany | europe | $380 | ~10h |
| PRGPrague | Czech Republic | europe | $381 | ~10h |
| NCENice | France | europe | $381 | ~10h |
| RIXRiga | Latvia | europe | $383 | ~10h |
| LEDSt. Petersburg | Russia | europe | $385 | ~10h |
| VCEVenice | Italy | europe | $392 | ~10h |
| WAWWarsaw | Poland | europe | $393 | ~10h |
| FLRFlorence | Italy | europe | $394 | ~10h |
| VIEVienna | Austria | europe | $395 | ~10h |
| VNOVilnius | Lithuania | europe | $395 | ~10h |
| LJULjubljana | Slovenia | europe | $396 | ~10h |
| KRKKrakow | Poland | europe | $397 | ~10h |
| BTSBratislava | Slovakia | europe | $397 | ~10h |
| ZAGZagreb | Croatia | europe | $402 | ~11h |
| FCORome | Italy | europe | $404 | ~11h |
| BUDBudapest | Hungary | europe | $406 | ~11h |
| SPUSplit | Croatia | europe | $411 | ~11h |
| NAPNaples | Italy | europe | $415 | ~11h |
| SVOMoscow | Russia | europe | $416 | ~11h |
| SJJSarajevo | Bosnia and Herzegovina | europe | $417 | ~11h |
| BEGBelgrade | Serbia | europe | $419 | ~11h |
| DBVDubrovnik | Croatia | europe | $421 | ~11h |
| TGDPodgorica | Montenegro | europe | $425 | ~11h |
| TIATirana | Albania | europe | $431 | ~11h |
| MLTMalta | Malta | europe | $434 | ~11h |
| SKPSkopje | North Macedonia | europe | $434 | ~11h |
| OTPBucharest | Romania | europe | $437 | ~11h |
| SOFSofia | Bulgaria | europe | $437 | ~11h |
| SKGThessaloniki | Greece | europe | $444 | ~12h |
| ATHAthens | Greece | europe | $458 | ~12h |
| ISTIstanbul | Turkey | europe | $459 | ~12h |
| SAWIstanbul Sabiha | Turkey | europe | $462 | ~12h |
| MYKMykonos | Greece | europe | $465 | ~12h |
| JTRSantorini | Greece | europe | $470 | ~12h |
| AYTAntalya | Turkey | europe | $484 | ~13h |
| LCALarnaca | Cyprus | europe | $501 | ~13h |
| NRTTokyo | Japan | asia | $579 | ~14h |
| HNDTokyo Haneda | Japan | asia | $582 | ~14h |
| TLVTel Aviv | Israel | middle east | $596 | ~13h |
| KIXOsaka | Japan | asia | $600 | ~14h |
| ICNSeoul | South Korea | asia | $604 | ~14h |
| PEKBeijing | China | asia | $607 | ~14h |
| PVGShanghai | China | asia | $651 | ~15h |
| TPETaipei | Taiwan | asia | $688 | ~16h |
| DELDelhi | India | asia | $690 | ~16h |
| KTMKathmandu | Nepal | asia | $703 | ~16h |
| CANGuangzhou | China | asia | $714 | ~16h |
| SZXShenzhen | China | asia | $717 | ~17h |
| HKGHong Kong | Hong Kong | asia | $719 | ~17h |
| HANHanoi | Vietnam | asia | $738 | ~17h |
| BOMMumbai | India | asia | $743 | ~17h |
| MNLManila | Philippines | asia | $751 | ~17h |
| CNXChiang Mai | Thailand | asia | $759 | ~17h |
| VTEVientiane | Laos | asia | $762 | ~17h |
| CEBCebu | Philippines | asia | $767 | ~18h |
| DADDa Nang | Vietnam | asia | $767 | ~18h |
| RGNYangon | Myanmar | asia | $773 | ~18h |
| BLRBangalore | India | asia | $787 | ~18h |
| REPSiem Reap | Cambodia | asia | $789 | ~18h |
| BKKBangkok | Thailand | asia | $791 | ~18h |
| MAAChennai | India | asia | $792 | ~18h |
| PNHPhnom Penh | Cambodia | asia | $800 | ~18h |
| SGNHo Chi Minh City | Vietnam | asia | $802 | ~18h |
| HKTPhuket | Thailand | asia | $828 | ~19h |
| CMBColombo | Sri Lanka | asia | $828 | ~19h |
| MLEMale | Maldives | asia | $836 | ~19h |
| PENPenang | Malaysia | asia | $844 | ~19h |
| KULKuala Lumpur | Malaysia | asia | $858 | ~20h |
| SINSingapore | Singapore | asia | $864 | ~20h |
| DPSBali | Indonesia | asia | $901 | ~20h |
| CGKJakarta | Indonesia | asia | $906 | ~21h |
Featured Deals from Chicago
Best Time to Fly from Chicago
Based on seasonal patterns across popular destinations, the best months to find deals from Chicago are typically January, February, March, April.
These months tend to offer the best combination of good weather at your destination and lower airfare demand. Set price alerts for your preferred routes to get notified when prices drop.
About O'Hare International
ORD — O'Hare International
Frequently Asked Questions
What are the cheapest international flights from Chicago?
Some of the most affordable international destinations from Chicago include Monterrey (est. $111 RT), Nassau (est. $111 RT), Cancun (est. $122 RT). Prices vary by season and how far in advance you book.
When is the best time to fly from Chicago?
Based on seasonal patterns, the best months to find deals from Chicago are typically January, February, March, April. These periods tend to offer a balance of favorable weather at popular destinations and lower demand for flights.
How far in advance should I book flights from Chicago?
For international flights from Chicago, booking 6–12 weeks in advance typically yields the best prices. For peak summer travel (June–August) and holiday periods, booking 3–6 months early is recommended. Setting a price alert lets you monitor fares automatically.
What airports serve Chicago?
Chicago is served by O'Hare International (ORD).
How many international destinations can I fly to from Chicago?
You can fly from Chicago to 125+ international destinations tracked by Wildly. These span regions including Europe, Asia, the Caribbean, South America, and beyond. Browse all routes to find and set alerts for your target destination.
Flights from Chicago by Budget
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Flights from Chicago by Region
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