Chicago Flight Deals: Phoenix from $28, Miami from $34 + Escape the Cold ❄️

Your weekly roundup of the best flight deals from Chicago's airports! This week features incredible domestic escapes, warm winter getaways, and premium cabin deals. All prices are round-trip from O'Hare (ORD) and Midway (MDW).

Escape the Chicago cold with these warm getaways departing in the coming weeks:

ORD → Miami - $34 round-trip

20°C average - Beach weather without the flight time. Direct flights available. May 2-7.

ORD → Cancun - $92 round-trip

24°C average - Beach paradise with warm Caribbean waters. Direct flights. Feb 9-14.

ORD → Punta Cana - $103 round-trip

26°C average - Dominican Republic beach resorts. Direct flights. Apr 11-16.

ORD → Montego Bay - $145 round-trip

27°C average - Jamaica sunshine and reggae vibes. Direct flights. Feb 16-21.

MDW → Phoenix - $28 round-trip

Multiple Airlines. Mar 1-6 (5 days). Direct. 83% below typical price!

Best dates to fly:

ORD → Miami - $34 round-trip

Multiple Airlines. May 2-7 (5 days). Direct. Perfect beach weather escape!

ORD → Los Angeles - $64 round-trip

Multiple Airlines. Mar 25-30 (5 days). Direct. 51% below typical.

MDW → Las Vegas - $80 round-trip

Multiple Airlines. Feb 22-27 (5 days). Direct. Around Presidents' Day.

ORD → Seattle - $89 round-trip

Multiple Airlines. Feb 12-17 (5 days). Direct. Returns on Presidents' Day.

ORD → San Francisco - $109 round-trip

Multiple Airlines. Feb 14-19 (5 days). Direct. Weekend departure near Presidents' Day.

ORD → Cancun - $92 round-trip

Multiple Airlines. Feb 9-14 (5 days). Direct. 63% below typical - beach paradise!

ORD → Punta Cana - $103 round-trip

Multiple Airlines. Apr 11-16 (5 days). Direct. Dominican Republic beach resorts.

ORD → Montego Bay - $145 round-trip

Multiple Airlines. Feb 16-21 (5 days). Direct. Jamaica sunshine - 64% savings!

ORD → London Heathrow - $375 round-trip

Multiple Airlines. Feb 1-4 (3 days). Direct. Next week departure!

ORD → Dublin - $375 round-trip

Multiple Airlines. Feb 1-4 (3 days). Direct. Ireland for less than coast-to-coast!

ORD → Barcelona - $375 round-trip

Multiple Airlines. Apr 15-18 (3 days). Direct. Mediterranean beaches - 34% below typical!

ORD → Madrid - $375 round-trip

Multiple Airlines. Feb 3-6 (3 days). Direct. 43% savings!

ORD → Paris - $394 round-trip

Multiple Airlines. Feb 1-4 (3 days). Direct. City of Light awaits!

ORD → Rome - $395 round-trip

Multiple Airlines. Feb 22-25 (3 days). Direct. 57% below typical - incredible deal!

ORD → Amsterdam - $395 round-trip

Multiple Airlines. Feb 19-22 (3 days). Direct. Canal-side adventures!

ORD → Lisbon - $412 round-trip

Multiple Airlines. Feb 1-4 (3 days). Direct. Mild weather year-round!

ORD → Delhi - $326 round-trip

Multiple Airlines. Feb 9-14 (5 days). Direct. Best in cooler winter months - 38% savings!

ORD → Tokyo Narita - $470 round-trip

Multiple Airlines. Apr 7-12 (5 days). Direct. Spring cherry blossoms - 55% below typical!

ORD → Tokyo Haneda - $520 round-trip

Multiple Airlines. Apr 6-11 (5 days). Direct. Convenient Haneda airport access.

ORD → Hong Kong - $597 round-trip

Multiple Airlines. Feb 5-10 (5 days). Direct. Best in cooler months.

ORD → Toronto - $86 round-trip

Multiple Airlines. Feb 12-17 (5 days). Direct. Quick weekend escape to Canada!

ORD → Dubai - $586 round-trip

Multiple Airlines. Feb 8-13 (5 days). Direct. Desert warmth and luxury - 19°C average!

💡 Chicago Airport Tip: O'Hare offers significantly more international connections, while Midway excels at domestic budget routes. For warm winter escapes, book 6-8 weeks in advance for best pricing!

Fly in luxury for less! This week's premium cabin deals feature incredible savings on Business Class to Europe, Asia, and beyond.

ORD → Seattle - $264 Business Class round-trip

Multiple Airlines. Mar 4-9 (5 days). Direct. 21% below typical ($264-$405 typical range). This is exceptional pricing for West Coast Business Class!

ORD → Miami - $329 Business Class round-trip

Multiple Airlines. Feb 24 - Mar 1 (5 days). Direct. 45% below typical - usually $329-$868! Warm escape in Business Class comfort.

ORD → San Francisco - $388 Business Class round-trip

Multiple Airlines. Feb 14-19 (5 days). Direct. 30% below typical pricing. Weekend departure near Presidents' Day.

ORD → Los Angeles - $404 Business Class round-trip

Multiple Airlines. Feb 14-19 (5 days). Direct. 24% savings on LAX Business Class.

ORD → Cancun - $308 Business Class round-trip

Multiple Airlines. Feb 24 - Mar 1 (5 days). Direct. 62% below typical ($308-$1,320 typical range)! Beach paradise with warm Caribbean waters in Business Class luxury. This is an exceptional deal - normally over $1,000!

ORD → San Juan - $413 Business Class round-trip

Multiple Airlines. Feb 16-21 (5 days). Direct. 40% below typical - Puerto Rico in style!

ORD → Montego Bay - $440 Business Class round-trip

Multiple Airlines. Apr 19-24 (5 days). Direct. Jamaica sunshine with Business Class service - 26% savings!

ORD → Punta Cana - $519 Business Class round-trip

Multiple Airlines. Feb 15-20 (5 days). Direct. 67% below typical ($519-$2,618 range)! Dominican Republic resorts in Business Class for a fraction of the usual cost.

ORD → Rome - $2,644 Business Class round-trip

Multiple Airlines. Mar 31 - Apr 3 (3 days). Direct. 40% below typical ($2,644-$6,234 range). Ancient Rome awaits in premium comfort - save almost $2,000!

ORD → Lisbon - $2,929 Business Class round-trip

Multiple Airlines. Feb 1-4 (3 days). Direct. 13% below typical - Portuguese adventures in Business Class!

ORD → Amsterdam - $3,066 Business Class round-trip

Multiple Airlines. Apr 22-25 (3 days). Direct. 10% below typical pricing for Business Class to Amsterdam.

ORD → Dublin - $3,449 Business Class round-trip

Multiple Airlines. Feb 24-27 (3 days). Direct. 42% below typical ($3,449-$8,354 range). Ireland in Business Class for half price - save over $2,400!

ORD → Paris - $3,467 Business Class round-trip

Multiple Airlines. Mar 17-20 (3 days). Direct. 38% below typical - experience Paris in luxury for $3,467 instead of $7,794!

ORD → Tokyo Narita - $3,134 Business Class round-trip

Multiple Airlines. Apr 23-28 (5 days). Direct. 25% below typical ($3,134-$5,204 typical range). Experience Japan's cherry blossoms in Business Class comfort!

ORD → Tokyo Haneda - $3,134 Business Class round-trip

Multiple Airlines. Apr 23-28 (5 days). Direct. Same great price to Haneda - 13% below typical!

ORD → Delhi - $3,152 Business Class round-trip

Multiple Airlines. Feb 11-16 (5 days). Direct. 37% below typical ($3,152-$6,852 typical). Explore India in Business Class - save over $1,850!

ORD → Seoul - $3,431 Business Class round-trip

Multiple Airlines. Feb 5-10 (5 days). Direct. 65% below typical ($3,431-$16,314 typical range)! This is an incredible Business Class deal to South Korea - usually over $16,000!

ORD → Hong Kong - $4,188 Business Class round-trip

Multiple Airlines. Feb 5-10 (5 days). Direct. 12% below typical for Hong Kong Business Class.

ORD → Dubai - $4,418 Business Class round-trip

Multiple Airlines. Feb 16-21 (5 days). Direct. 46% below typical ($4,418-$11,846 typical). Desert luxury and warmth in Business Class - save over $3,700!

ORD → Tel Aviv - $4,459 Business Class round-trip

Multiple Airlines. Feb 5-10 (5 days). Direct. 20% below typical - Israel in Business Class comfort!

Best Airport for Europe: O'Hare dominates with direct flights to London, Paris, Dublin, Rome, Amsterdam, and more. All major European destinations are best served from ORD.

Best Airport for Budget Domestic: Midway offers fantastic Southwest deals to Phoenix and Las Vegas. Check both airports for West Coast routes - competition keeps prices low.

Best Airport for Asia: O'Hare is your only option with direct service to Tokyo, Hong Kong, Seoul, Delhi, and more. Business Class to Asia from Chicago offers exceptional value right now.

Best Airport for Caribbean: O'Hare wins with direct service to Cancun, Punta Cana, Montego Bay, and San Juan. Winter warm escapes are trending 50-65% below typical prices!

Transit Tip: O'Hare's Blue Line train connection makes it accessible from downtown in 45 minutes for $5. Midway's Orange Line takes 30 minutes. For early morning international flights from O'Hare, consider staying near the airport the night before.

Hidden Gem: Toronto (YYZ) from O'Hare at $86 makes a perfect weekend getaway and can serve as a positioning flight for cheaper trans-Atlantic routes on Air Canada.

💡 Pro Tip: Business Class deals to Asia and Europe rarely drop this low. The Seoul deal at $3,431 (usually $16,314) and the Cancun Business Class at $308 (usually $1,320) are exceptional opportunities. Book quickly as premium cabin inventory at these prices goes fast!

Safe travels from the Windy City! ✈️