Best Flights starting from $344
from$344economy
Chicago (ORD)
Sat, Jun 20
Roundtrip
Key West (EYW)
Tue, Jun 23
from$368economy
Chicago (ORD)
Tue, Jun 16
Roundtrip
Key West (EYW)
Fri, Jun 19
from$384economy
Chicago (ORD)
Mon, Jun 15
Roundtrip
Key West (EYW)
Thu, Jun 18
from$384economy
Chicago (ORD)
Wed, Jun 17
Roundtrip
Key West (EYW)
Sat, Jun 20
from$449economy
Chicago (ORD)
Fri, Jun 19
Roundtrip
Key West (EYW)
Mon, Jun 22
from$459economy
Chicago (ORD)
Sun, Jun 21
Roundtrip
Key West (EYW)
Wed, Jun 24
from$466economy
Chicago (ORD)
Thu, Jun 18
Roundtrip
Key West (EYW)
Sun, Jun 21
Fields updated — click View Prices to search ↑
Other Options for This Route
Other Destinations
Chicago (ORD) to Las Vegas (LAS) in June from $102
From $102
Chicago (ORD) to Las Vegas (Any) in June from $131
From $131
Chicago (ORD) to Miami (MIA) in June from $148
From $148
Chicago (ORD) to Seattle (SEA) in June from $148
From $148
Chicago (ORD) to Salt Lake City (SLC) in June from $169
From $169
Chicago (ORD) to Fort Myers (RSW) in June from $176
From $176
Flights from Other Cities
Newark (EWR) to Key West (EYW) in June from $349
From $349
Cincinnati (Any) to Key West (EYW) in June from $433
From $433
Cleveland (CLE) to Key West (EYW) in September from $381
From $381
Manchester (MHT) to Key West (EYW) in October from $427
From $427
Charlotte (CLT) to Key West (EYW) in October from $449
From $449
Missoula (MSO) to Key West (EYW) in October from $557
From $557
✈️ Flight Guide: Chicago (ORD) → Key West (EYW)
Complete travel information for your June journey
Departing from Chicago (ORD) FAQs
Key West International Airport (EYW) is mainly served by regional and major carriers offering economy fares, including Silver Airways and American Airlines seasonal or connecting services. For the cheapest economy flights from Key West, compare fares on Google Flights, Kayak, and airline websites and book 3–8 weeks in advance for the best low-cost options. Consider nearby airports like Miami and Fort Lauderdale for additional budget routes.
In March, book early and be flexible with midweek travel to secure the cheapest economy fares from Key West International Airport (EYW). Use fare alerts and check connecting options via Miami (MIA) or Fort Lauderdale (FLL) for lower-priced economy tickets; March is peak spring-break season so prices can rise — booking 4–8 weeks in advance often helps. Sign up for price drop alerts to snag last-minute deals.
Though small, Key West International Airport (EYW) connects travelers to major Florida hubs: Miami (Miami International Airport), Fort Lauderdale (Fort Lauderdale-Hollywood International), Orlando, Tampa, and West Palm Beach. Visitors also often connect onwards to Havana (Cuba historically), Nassau (Bahamas), and mainland Gulf Coast destinations like Naples and Fort Myers via regional connections.
Early morning and late evening departures are typically the cheapest times to fly economy from Key West International Airport (EYW) because they are less popular with leisure travelers. Midweek flights (Tuesdays and Wednesdays) usually offer lower economy fares than weekend travel. Use flexible-date search tools and look at nearby airports for alternative low-cost departure times.
Cheapest economy fares often exclude checked baggage and seat selection; travelers flying from Key West International Airport (EYW) should review the airline’s basic economy rules before booking. Expect carry-on allowances but check the carrier’s website for exact dimensions and fees for checked bags; purchasing baggage online in advance usually saves money compared with airport rates. Consider bundling with a small personal item if you want to avoid extra charges.
November often brings shoulder-season discounts on economy travel from Key West International Airport (EYW) after the fall events and before peak winter holidays, especially mid-November. Watch for carrier flash sales and sign up for airline newsletters to catch promotional economy fares; booking 2–6 weeks out during mid-November can yield good bargains. Check major OTAs and airline pages for limited-time deals.
Arriving at Key West (EYW) FAQs
Arriving on an 'Economy Class - Cheapest (ECONOMY)' fare typically means the lowest-priced economy ticket with restrictions like limited or no seat selection and possible baggage fees. These cheapest economy arrivals prioritize price over flexibility; check the airline’s baggage and change policies before booking to avoid extra charges. For better value, compare bundled economy options that include checked baggage.
Cheapest economy arrivals booked from Key West International Airport (EYW) frequently connect to Miami (Miami International Airport), Fort Lauderdale (Fort Lauderdale-Hollywood International), Orlando, Tampa, and West Palm Beach. Travelers also use economy connections to reach Nassau (Bahamas) or mainland Florida Gulf Coast cities like Naples and Fort Myers via hub transfers.
In July, search early and be flexible with dates to find the cheapest economy arrival options from Key West International Airport (EYW). Compare connecting itineraries via Miami or Fort Lauderdale and consider midweek departures; booking 6–10 weeks in advance helps during summer peaks. Use multi-search engines and set fare alerts to track price drops.
Yes — cheapest economy arrival tickets usually limit amenities: no assigned seats until check-in, possible carry-on restrictions on some carriers, and fewer onboard perks. Arrival procedures like customs and baggage claim remain the same, but priority baggage and lounge access are typically excluded. Read the fare rules closely to understand arrival-related limitations.
Often it is cheaper to arrive at major hubs like Miami (Miami International Airport) or Fort Lauderdale (Fort Lauderdale-Hollywood International) instead of direct small-airport arrivals when searching for the cheapest economy fares. Larger airports have more competition and flight frequency, which drives down prices; you can then transfer to your final destination by local carrier, shuttle, or rental car. Compare total travel time and transfer costs when choosing this strategy.
When arriving on a cheapest economy fare, check baggage claim policies and be ready with the correct carry-on or checked bag receipts to avoid fees. Have digital copies of boarding passes and travel documents, arrive early for connections, and research ground transport options beforehand to avoid high airport transport costs. Consider pre-booking baggage or seat upgrades online for a lower rate than airport counters.
1.0.2602.25
Events and Festivals Impacting Economy Fares at Key West International Airport (EYW)
Events like Fantasy Fest (late October), Hemingway Days (July), and the Key West Food and Wine Festival (often spring) drive up demand and raise economy fares into Key West International Airport (EYW). To find the cheapest economy tickets around these events, book well in advance or travel on the event’s fringe dates. Consider flying into Miami or Fort Lauderdale and transferring if direct event-period fares to Key West are prohibitively expensive. CTA: Check event dates before booking and compare economy fares across nearby airports to save.
Best Time to Fly Economy from Key West International Airport (EYW)
The best time to fly economy from Key West International Airport (EYW) for lowest fares is during shoulder seasons (late April–early June, September–early November) and midweek days (Tuesday–Thursday). For holiday travel, book 2–3 months in advance; for off-peak months, 3–6 weeks can be sufficient. Use fare alerts and compare alternate hub arrivals (Miami or Fort Lauderdale) to increase chances of finding the cheapest economy fares. CTA: Set a fare alert today to know when cheap economy tickets from Key West become available.
Direct vs. Connecting Economy Flights from Key West International Airport (EYW)
Direct flights from Key West International Airport (EYW) can be faster and more convenient but often cost more than connecting itineraries. Connecting flights via Miami (MIA), Fort Lauderdale (FLL), or Orlando (MCO) commonly provide cheaper economy fares due to higher competition and more flight options. When choosing cheapest economy options, factor in connection time, potential baggage transfer fees, and total door-to-door travel time. If convenience is paramount and budget allows, choose a nonstop; if price is the priority, select well-timed connections. CTA: Compare direct and connecting options on fare comparison sites to determine the best economy route for your trip.
Airline Comparison for Economy Travel from Key West International Airport (EYW)
Major carriers and regionals serving Key West International Airport (EYW), such as Silver Airways and American Airlines (through connections), offer different economy options. Silver Airways commonly provides regional routes with transparent base fares but limited frills, while major carriers may offer more connectivity and loyalty benefits but sometimes higher base prices. For the cheapest economy fares, compare total cost including baggage and seat fees, and check multi-airline itineraries. CTA: Use a fare comparison tool to evaluate total economy costs across carriers and secure the best-value ticket.
Seasonal Travel Tips for Cheapest Economy Flights to/from Key West International Airport (EYW)
Winter (Dec–Feb): High demand increases economy fares; book early for the cheapest seats and consider mid-January for lower prices. Spring (Mar–May): Peak spring-break periods raise prices in March; aim for April for better economy deals. Summer (Jun–Aug): Early booking is essential; consider alternative hubs to lower economy ticket costs. Fall (Sep–Nov): Shoulder season can yield bargains, but watch hurricane season timing and have flexible tickets. Always verify airline baggage rules and pre-pay bags online where possible to lock in lower fees. CTA: For the best cheapest-economy experience, sign up for seasonal fare alerts and check nearby hubs before you buy.
Flight Time and Schedules for Key West International Airport (EYW) — Economy Options
Flight times from Key West International Airport (EYW) to nearby hubs are short: Key West to Miami (Miami International Airport) is roughly 35–45 minutes nonstop, while connections to Orlando (Orlando International) or Tampa (Tampa International) via hubs typically range from 2–4 hours including a short connection. Economy schedules tend to concentrate on morning and late afternoon departures to maximize regional connectivity. For the cheapest economy itineraries, look for red-eye or early-morning schedules when fewer travelers are booked. CTA: Check up-to-date schedules on airline websites or Google Flights to plan an economy trip from Key West.
Cheap Flights from Key West International Airport (EYW) — Economy Fare Strategies
To find the cheapest economy flights from Key West International Airport (EYW), use flexible-date searches, set fare alerts on Google Flights and Kayak, and compare itineraries that route through high-competition hubs like Miami (Miami International Airport) and Fort Lauderdale (Fort Lauderdale-Hollywood International). Consider booking basic economy for short trips, but factor in baggage and seat fees to evaluate total cost. Use midweek travel and off-peak times to secure the best deals, and consider nearby airports if drive or shuttle transfers reduce overall expenses. CTA: Search cheap flights from Key West now and activate fare alerts to catch the next economy sale.