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Lowest Estimated Prices from Chicago
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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 Route Estimates 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. Fare reviews and notifications are paused while the fare feed moves to a new provider.
About O'Hare International
O'Hare is United's second-largest hub after Houston, making it a powerhouse for transatlantic and transpacific flights. You'll find competitive pricing on European routes because United, American, and Delta all fight for market share here. The airport is modernizing aggressively—the new Terminal 5 (opened 2024) is genuinely pleasant, though older terminals still have the tired-airport vibe. O'Hare handles 84+ million passengers annually, so expect crowds during peak hours (6-9am, 4-7pm), but the airport's been investing in TSA PreCheck lanes and Clear kiosks, making security manageable if you're enrolled.
Terminals & Airlines
Terminal 1 (American/partners), Terminal 2 (international carriers including Lufthansa, Air France, British Airways, Swiss), Terminal 3 (United hub—massive, confusing, but has best food options), Terminal 5 (new, modern, houses some United flights and partners), Terminal C (regional/low-cost carriers, Southwest when it operates). Terminal 2 is worth targeting for European carriers—newer, less chaotic. Terminal 3 is unavoidable for most United flights but plan extra time for connections.
Getting to the Airport
CTA Blue Line (24/7, $5 one-way, 40-45 min from Loop/downtown Chicago during normal traffic, often faster than driving)—board at any downtown station, runs directly to all terminals. Rideshare (Uber/Lyft, $28-42 during off-peak, $50-75 during rush hour 6-10am or 3-7pm from downtown, 25-40 min depending on traffic). Taxi flat rate $42 from downtown Loop, 35-50 min. Rental car pickup in Terminal 1 or off-site shuttles available. Best option: CTA Blue Line if traveling light and flexible on time; Uber/Lyft if arriving after 10pm when Blue Line gets sketchy.
Parking
Economy Lot A/B: $17/day (10-min walk or free shuttle). Garage parking (covered): $19/day. Valet at terminal: $32/day. Pro move: book through SpotHero or ParkWhiz 2+ weeks ahead for $8-12/day at nearby off-airport lots with free airport shuttle—saves $5-10/day and less hassle than economy lot. Cell phone lot is free for 15 min while waiting for pickup.
Airlines at ORD
Pro Tips for Flying from Chicago
United runs 3+ daily flights to London (LHR, LGW, STN) from ORD—prices are genuinely competitive because American and Delta also fly the route heavily. Check all three London airports before booking; Stansted is sometimes $80-120 cheaper but adds an hour to ground transport.
ORD to Dublin (DUB) is a sweet spot: 5-6 daily flights across United/American/Aer Lingus, and the route rarely gets expensive. Book 4-6 weeks ahead and you'll find sub-$400 roundtrip transatlantic fares regularly.
Terminal 3 (United) has a hidden gem: the United Club in concourse B has shower suites ($35 for 60 min, free for Elite members). If you have a long layover on a hot day, it's worth the cost.
Finnair and other Nordic carriers use ORD heavily for Asia connections via Helsinki—often cheaper than United's Asia routes, especially to Tokyo and Bangkok. Compare Finnair/ANA joint fares before assuming United is the best option.
The TSA PreCheck line at ORD in Terminal 3 can still hit 20+ min during 6-9am. If not Pre/Clear enrolled, fly out 11am-2pm or after 7pm for sub-10 min security waits.
Cheapest Regions from Chicago
| Region | Est. Avg Price | Best Month |
|---|---|---|
| mexico | $280 | september |
| caribbean | $320 | august |
| central America | $340 | september |
| europe | $480 | may |
| south America | $580 | april |
| middle East | $620 | october |
| asia | $650 | september |
| africa | $750 | november |
| oceania | $820 | september |
Nearby Airports to Consider
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. Fare reviews and notifications are paused during the provider migration.
What airports serve Chicago?
Chicago is served by O'Hare International (ORD).
How many international destinations can I fly to from Chicago?
Wildly lists 125+ international destinations from Chicago. These span regions including Europe, Asia, the Caribbean, South America, and beyond. Browse all routes to find your target destination.
Flights from Chicago by Budget
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Flights from Chicago by Region
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