Miami Flight Deals - Chicago from $28 Round-Trip + Caribbean, Europe & More

This week's best flight deals from MIA and FLL - San Juan from $61, Barcelona from $261, and exclusive Business Class deals for Premium members

February 27, 2026

Your weekly roundup of the best flight deals from Miami International (MIA) and Fort Lauderdale (FLL) - February 26, 2026. This week is packed with standout deals, led by an almost unbelievable $28 round-trip to Chicago. Whether you are dreaming of Caribbean beaches, a European city break, or a quick domestic getaway, we have got deals across every region departing from your doorstep. Free members get full access to all Economy budget deals below. Premium members unlock Business Class fares, error fares, and our Miami airport strategy guide - scroll down to see what you are missing.

✈️ This Week's Headline Deal

Stop everything. MIA → Chicago (ORD) is showing at just $28 round-trip - that is 69% below typical pricing. Depart Apr 23, return Apr 28 (5 nights midweek). Multiple airlines, direct flight. This is one of the cheapest domestic fares we have ever seen out of Miami. Book before it disappears.

Best dates to fly: - Apr 23 - Apr 28 | $28 | 5 days - Apr 23 - Apr 30 | $28 | 7 days - Apr 23 - May 3 | $28 | 10 days

🇺🇸 Domestic US Deals

Great news for domestic travelers - both Chicago and New York are showing unusually low fares from MIA this week. These are direct flights, so no layover hassle.

MIA → Chicago (ORD) - $28 round-trip - Multiple Airlines. Apr 23 - Apr 28. Direct. ✅ Good Deal (69% below typical)

MIA → New York JFK - $35 round-trip - Multiple Airlines. Mar 18 - Mar 23 (in 2 weeks). Direct. ✅ Good Deal (86% below typical)

MIA → Los Angeles (LAX) - $359 round-trip - Multiple Airlines. Mar 14 - Mar 19. Weekend departure (Saturday). Direct. ✅ Good Deal

Best dates for New York JFK:

Mar 18 - Mar 23 | $35 | 5 days
Mar 18 - Mar 25 | $35 | 7 days
Mar 18 - Mar 28 | $35 | 10 days

🌴 Caribbean and Latin America

Miami is one of the best airports in the US for Caribbean flights - short flights, tons of competition, and prices to match. This week we are seeing deals to San Juan, Nassau, Punta Cana, Cancun, Montego Bay, Barbados, Bogota, Aruba, Lima, Sao Paulo, Santiago, and Buenos Aires. Here are the standout Economy fares:

FLL → San Juan (SJU) - $61 round-trip - Multiple Airlines. Apr 11 - Apr 16. Weekend departure (Saturday). Direct. ✅ Good Deal (47% below typical)

MIA → San Juan (SJU) - $65 round-trip - Multiple Airlines. Mar 16 - Mar 21 (in 2 weeks). Direct. ✅ Good Deal (50% below typical)

MIA → Nassau (NAS) - $90 round-trip - Multiple Airlines. Mar 17 - Mar 22 (in 2 weeks). Direct. ✅ Good Deal (40% below typical)

FLL → Nassau (NAS) - $90 round-trip - Multiple Airlines. Mar 12 - Mar 17 (in 2 weeks). Direct. ✅ Good Deal (23% below typical)

MIA → Punta Cana (PUJ) - $94 round-trip - Multiple Airlines. Mar 23 - Mar 28 (in 3-4 weeks). 26C at destination. Direct. ✅ Good Deal (26% below typical)

FLL → Cancun (CUN) - $109 round-trip - Multiple Airlines. Mar 12 - Mar 17 (in 2 weeks). 25C beach paradise. Direct. ✅ Good Deal (33% below typical)

MIA → Montego Bay (MBJ) - $118 round-trip - Multiple Airlines. Mar 16 - Mar 21 (in 2 weeks). 27C Jamaica sunshine. Direct. ✅ Good Deal (29% below typical)

MIA → Cancun (CUN) - $142 round-trip - Multiple Airlines. Mar 22 - Mar 27 (in 3-4 weeks). Weekend departure (Sunday). Direct. ✅ Good Deal (30% below typical)

MIA → Barbados (BGI) - $305 round-trip - Multiple Airlines. Mar 15 - Mar 20 (in 2 weeks). Weekend departure (Sunday). 26C year-round tropical warmth. Direct. ✅ Good Deal (6% below typical)

MIA → Bogota (BOG) - $130 round-trip - Multiple Airlines. Mar 17 - Mar 22 (in 2 weeks). Direct. ✅ Good Deal (41% below typical)

MIA → Aruba (AUA) - $208 round-trip - Multiple Airlines. Apr 14 - Apr 19 (in 1-2 months). Direct. ✅ Good Deal (20% below typical)

MIA → Lima (LIM) - $247 round-trip - Multiple Airlines. Mar 26 - Mar 31 (in 3-4 weeks). Direct. ✅ Good Deal (18% below typical)

MIA → Sao Paulo (GRU) - $254 round-trip - Multiple Airlines. May 13 - May 18 (in 2-3 months). Direct. ✅ Good Deal (48% below typical)

MIA → Santiago (SCL) - $292 round-trip - Multiple Airlines. Apr 29 - May 4 (in 2-3 months). Direct. ✅ Good Deal (23% below typical)

MIA → Buenos Aires (EZE) - $344 round-trip - Multiple Airlines. Mar 15 - Mar 20 (in 2 weeks). Weekend departure (Sunday). Direct. ✅ Good Deal (32% below typical)

Many of these Caribbean routes are also bookable with miles. Award Travel Finder tracks the best award redemptions daily - so if you have points sitting around, check if you can do even better than these cash prices.

🇪🇺 Europe

MIA has strong transatlantic connections and this week Europe is delivering. Barcelona leads the pack at just $261 - that is a jaw-dropping price for a transatlantic round-trip. Spring in Europe is calling.

MIA → Barcelona (BCN) - $261 round-trip - Multiple Airlines. Apr 15 - Apr 18 (in 1-2 months). Direct. ✅ Good Deal (50% below typical)

MIA → Madrid (MAD) - $354 round-trip - Multiple Airlines. Apr 13 - Apr 16 (in 1-2 months). Direct. ✅ Good Deal (22% below typical)

MIA → London Heathrow (LHR) - $439 round-trip - Multiple Airlines. Mar 17 - Mar 20 (in 2 weeks). Direct. ✅ Good Deal (36% below typical)

MIA → Paris (CDG) - $459 round-trip - Multiple Airlines. Mar 22 - Mar 25 (in 3-4 weeks). Weekend departure (Sunday). Direct. ✅ Good Deal (27% below typical)

MIA → Amsterdam (AMS) - $684 round-trip - Multiple Airlines. Apr 19 - Apr 22 (in 1-2 months). Weekend departure (Sunday). Direct. ✅ Good Deal (14% below typical)

MIA → Frankfurt (FRA) - $714 round-trip - Multiple Airlines. May 5 - May 8 (in 2-3 months). Direct. ✅ Good Deal (41% below typical)

MIA → Zurich (ZRH) - $714 round-trip - Multiple Airlines. May 5 - May 8 (in 2-3 months). Direct. ✅ Good Deal (41% below typical)

Pro tip: MIA is far superior to FLL for transatlantic Europe routes. American Airlines, British Airways, Iberia, Lufthansa, and Air France all operate long-haul services out of Miami International. If you are chasing miles and points on European flights, Miles and Points Daily covers the best credit card bonuses to help you earn faster toward your next Europe trip.

🌏 Middle East

Two standout Economy deals to the Middle East this week - Dubai and Doha are both showing significantly below-typical pricing from MIA. Spring is actually a wonderful time to visit before the summer heat arrives.

MIA → Dubai (DXB) - $592 round-trip - Multiple Airlines. Mar 16 - Mar 21 (in 2 weeks). 20C - great time to visit. Direct. ✅ Good Deal (45% below typical)

MIA → Doha (DOH) - $695 round-trip - Multiple Airlines. Mar 16 - Mar 21 (in 2 weeks). 19C - ideal spring conditions. Direct. ✅ Good Deal (50% below typical)

MIA → Tel Aviv (TLV) - $804 round-trip - Multiple Airlines. Apr 21 - Apr 26 (in 1-2 months). Direct. ✅ Good Deal (41% below typical)

✈️ Miami Airport Tip

MIA (Miami International) is your best bet for Europe, Middle East, and South America - it has the widest selection of long-haul carriers and direct routes.
FLL (Fort Lauderdale) shines for Caribbean short-hauls and budget domestic routes - carriers like Spirit and Southwest operate heavily out of FLL, which drives prices down on routes like Nassau and San Juan.
This week FLL is offering competitive fares to San Juan ($61) and Nassau ($90) and Cancun ($109) that rival or beat MIA prices - worth checking both airports before you book.
Parking tip: FLL is generally cheaper for long-stay parking than MIA. If you are heading to Europe from MIA for 10+ days, factor that in.
MIA is a major American Airlines hub - if you collect AAdvantage miles, flights from MIA often earn bonus miles on AA metal.

Want to maximize the miles you earn on these flights? Award Travel Finder finds the best award flight and hotel redemptions daily - a great companion to this newsletter if you are building toward a Business Class redemption.

💼 Premium: Business Class and First Class Deals from Miami

This week is unusually strong for Business Class out of MIA. We are seeing deals across domestic, Caribbean, Latin America, Europe, and the Middle East - with some routes hitting 50-67% below typical Business Class pricing. Here are the best premium cabin deals available right now.

🇺🇸 Business Class - Domestic US

MIA → Chicago (ORD) - Business - $127 round-trip - Multiple Airlines. Apr 23 - Apr 28. Direct. 57% below typical (usually $127-$461). Best dates:

Apr 23 - Apr 28 | $127 | 5 days
Apr 23 - Apr 30 | $127 | 7 days
Apr 23 - May 3 | $127 | 10 days

MIA → New York JFK - Business - $134 round-trip - Multiple Airlines. Mar 25 - Mar 30 (in 3-4 weeks). Direct. 64% below typical (usually $134-$619). Best dates:

Mar 25 - Mar 30 | $134 | 5 days
Mar 25 - Apr 1 | $134 | 7 days
Mar 25 - Apr 4 | $134 | 10 days

MIA → Los Angeles (LAX) - Business - $699 round-trip - Multiple Airlines. Mar 24 - Mar 29 (in 3-4 weeks). Direct. 34% below typical (usually $699-$1429).

🌴 Business Class - Caribbean and Latin America

FLL → San Juan (SJU) - Business - $170 round-trip - Multiple Airlines. Apr 19 - Apr 24. Weekend departure (Sunday). Direct. 31% below typical (usually $170-$325).

MIA → San Juan (SJU) - Business - $194 round-trip - Multiple Airlines. Mar 17 - Mar 22 (in 2 weeks). Direct. 39% below typical (usually $194-$444).

MIA → Nassau (NAS) - Business - $210 round-trip - Multiple Airlines. Mar 17 - Mar 22 (in 2 weeks). Direct. 54% below typical (usually $210-$695). Outstanding value for Business Class.

MIA → Punta Cana (PUJ) - Business - $221 round-trip - Multiple Airlines. Jun 16 - Jun 21 (in 3 months). Direct. 39% below typical (usually $221-$499).

MIA → Montego Bay (MBJ) - Business - $253 round-trip - Multiple Airlines. Jun 14 - Jun 19 (in 3 months). Weekend departure (Sunday). 27C Jamaica sunshine. Direct. 29% below typical.

MIA → Cancun (CUN) - Business - $264 round-trip - Multiple Airlines. Mar 18 - Mar 23 (in 2 weeks). Direct. 42% below typical (usually $264-$641).

MIA → Bogota (BOG) - Business - $446 round-trip - Multiple Airlines. Mar 26 - Mar 31 (in 3-4 weeks). Direct. 22% below typical (usually $446-$702).

MIA → Aruba (AUA) - Business - $519 round-trip - Multiple Airlines. Apr 14 - Apr 19 (in 1-2 months). Direct. 30% below typical (usually $519-$957).

MIA → Lima (LIM) - Business - $1,224 round-trip - Multiple Airlines. Mar 12 - Mar 17 (in 2 weeks - act fast). Direct. 36% below typical (usually $1,224-$2,614).

MIA → Santiago (SCL) - Business - $2,064 round-trip - Multiple Airlines. May 27 - Jun 1 (near Memorial Day). Direct. 17% below typical (usually $2,064-$2,884).

MIA → Sao Paulo (GRU) - Business - $2,234 round-trip - Multiple Airlines. May 27 - Jun 1 (near Memorial Day). Direct. 28% below typical (usually $2,234-$4,004).

MIA → Buenos Aires (EZE) - Business - $2,242 round-trip - Multiple Airlines. Mar 14 - Mar 19 (in 2 weeks - act fast). Weekend departure (Saturday). Direct. 42% below typical (usually $2,242-$5,444). Savings of up to $1,601 vs typical pricing.

🇪🇺 Business Class - Europe

Europe Business Class from Miami is delivering some serious deals this week. Paris stands out with 51% savings vs typical pricing. These are the kind of deals where you want to have your miles and points strategy ready before you even pull out a credit card.

MIA → Madrid (MAD) - Business - $2,676 round-trip - Multiple Airlines. Mar 15 - Mar 18 (in 2 weeks - act fast). Weekend departure (Sunday). Direct. 20% below typical (usually $2,676-$4,000). Best dates:

Mar 15 - Mar 18 | $2,676 | 3 days
Mar 15 - Mar 19 | $2,676 | 4 days
Mar 15 - Mar 20 | $2,676 | 5 days

MIA → London Heathrow (LHR) - Business - $3,192 round-trip - Multiple Airlines. May 27 - May 30 (near Memorial Day). Direct. 19% below typical (usually $3,192-$4,642). Savings of $725 vs typical.

MIA → Paris (CDG) - Business - $3,464 round-trip - Multiple Airlines. Mar 31 - Apr 3 (in 1-2 months). Direct. 51% below typical (usually $3,464-$10,609). This is an exceptional saving of $3,573 vs typical pricing.

MIA → Amsterdam (AMS) - Business - $4,234 round-trip - Multiple Airlines. May 21 - May 24 (around Memorial Day). Direct.

MIA → Barcelona (BCN) - Business - $4,514 round-trip - Multiple Airlines. Apr 1 - Apr 4 (in 1-2 months). Direct. 39% below typical (usually $4,514-$10,269). Savings of $2,878.

MIA → Frankfurt (FRA) - Business - $5,927 round-trip - Multiple Airlines. Mar 31 - Apr 3 (in 1-2 months). Direct. 38% below typical (usually $5,927-$13,184). Savings of $3,629.

MIA → Zurich (ZRH) - Business - $5,927 round-trip - Multiple Airlines. Mar 31 - Apr 3 (in 1-2 months). Direct. 7% below typical (usually $5,927-$6,777).

🌍 Business Class - Middle East

The Dubai Business Class deal this week is genuinely remarkable - 67% below typical pricing is the kind of savings that only appears a handful of times a year on this route.

MIA → Dubai (DXB) - Business - $4,670 round-trip - Multiple Airlines. Mar 12 - Mar 17 (in 2 weeks - act fast). Direct. 67% below typical (usually $4,670-$23,484). That is a saving of up to $9,407. Extraordinary deal.

Best dates for MIA → Dubai Business: - Mar 12 - Mar 17 | $4,670 | 5 days - Mar 12 - Mar 19 | $4,670 | 7 days - Mar 12 - Mar 22 | $4,670 | 10 days

MIA → Tel Aviv (TLV) - Business - $5,240 round-trip - Multiple Airlines. Apr 21 - Apr 26 (in 1-2 months). Direct. 16% below typical (usually $5,240-$7,214).

MIA → Doha (DOH) - Business - $8,371 round-trip - Multiple Airlines. Jun 16 - Jun 21 (in 3 months). Direct. 1% below typical - note this is priced at typical levels, but listed for completeness.

✈️ Premium Miami Airport Strategies

MIA vs FLL - Which Airport for Which Route?

Europe and long-haul: Always check MIA first. American Airlines, British Airways, Lufthansa, Air France, Iberia, and Emirates all operate long-haul flights from Miami International. FLL has virtually no transatlantic competition.
Caribbean short-haul: Check BOTH airports. This week FLL is beating or matching MIA on San Juan, Nassau, and Cancun. Spirit, JetBlue, and Southwest operate heavily from FLL on Caribbean routes.
South America: MIA wins for direct flights - it is the premier hub for Latin American routes in the US. Copa, LATAM, Avianca, and American all fly South America routes primarily from MIA.
Middle East: MIA only. Emirates flies direct MIA-DXB and the Dubai Business Class deal this week is one of the best we have seen all year.
Domestic budget: FLL often beats MIA on domestic budget fares thanks to Spirit and Southwest. Always compare both.
Hidden gem route from MIA: The MIA to Bogota route is underrated for South America gateway trips - it is a short hop to Colombia and onward connections are plentiful.

Transit Tips

MIA tip: Terminal D and E are the main international departure terminals. American Airlines operates out of Terminal D for most long-haul and international flights. Allow extra time - MIA security can be slow during peak Caribbean travel windows (Friday afternoons, Sunday evenings).
FLL tip: A smaller airport with generally faster security. Rideshare pickup is in the garage across from Terminal 1. FLL is about 30 minutes north of Miami proper - factor this into your travel time.
Midweek departures: Both airports are significantly quieter Tuesday through Thursday. If your deal has flexible dates (and many this week do), midweek check-in is smoother.
FLL parking: Long-term parking at FLL averages $10-14 per day. MIA long-term runs $12-18 per day. For trips of 7 or more days, a rideshare or taxi often beats parking costs at MIA.
Connecting through Miami: MIA is one of the best connection airports in the country for Latin America and Caribbean routes. If you are positioning from another US city, MIA connections are frequent and reliable.

Thinking about using points for any of the Business Class deals above? Miles and Points Daily publishes daily credit card bonus updates and points strategies - essential reading if you are building toward a Business Class redemption on a route like Miami to Dubai or Miami to Paris.

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