Chicago Flight Deals: Phoenix from $28, Miami from $36 + Premium Business Class Steals

Your weekly roundup of the best flight deals from Chicago's airports. This week we found 55 incredible deals with savings up to 83% off typical prices. Whether you're planning a quick escape or dreaming of warmer destinations, we've got options from both O'Hare and Midway.

Escape the -4°C Chicago freeze with these warm getaways. All destinations offer 20°C+ sunshine and direct flights:

MDW → Phoenix - $28 round-trip with Multiple Airlines. Mar 2-7 (5 days). Direct flight. ✅ Good deal - 83% below typical.

Best dates to fly:

ORD → Miami - $36 round-trip with Multiple Airlines. Feb 23-28 (5 days). Direct flight. ✅ Good deal - 69% below typical. Perfect Presidents' Day getaway!

ORD → Los Angeles - $55 round-trip with Multiple Airlines. Mar 10-15 (5 days). Direct flight. ✅ Good deal - 57% below typical.

MDW → Las Vegas - $80 round-trip with Multiple Airlines. Feb 28-Mar 5 (5 days). Direct flight. ✅ Good deal - 52% below typical.

ORD → Seattle - $99 round-trip with Multiple Airlines. Feb 24-Mar 1 (5 days). Direct flight. ✅ Good deal - 41% below typical.

ORD → San Francisco - $109 round-trip with Multiple Airlines. Feb 21-26 (5 days). Direct flight. ✅ Good deal - 42% below typical.

ORD → Punta Cana - $88 round-trip with Multiple Airlines. Mar 9-14 (5 days). Direct flight. ✅ Good deal - 81% below typical. 26°C average - Perfect winter escape!

ORD → Cancun - $92 round-trip with Multiple Airlines. Apr 13-18 (5 days). Direct flight. ✅ Good deal - 40% below typical. 24°C average - Beach paradise!

ORD → San Juan - $100 round-trip with Multiple Airlines. Feb 16-21 (5 days). Direct flight. ✅ Good deal - 50% below typical.

ORD → Montego Bay - $145 round-trip with Multiple Airlines. Mar 8-13 (5 days). Direct flight. ✅ Good deal - 62% below typical. 27°C average - Jamaica sunshine!

ORD → Paris - $394 round-trip with Multiple Airlines. Feb 8-11 (3 days). Direct flight. ✅ Good deal - 13% below typical.

ORD → Amsterdam - $395 round-trip with Multiple Airlines. Feb 26-Mar 1 (3 days). Direct flight. ✅ Good deal - 31% below typical.

ORD → Dublin - $396 round-trip with Multiple Airlines. Mar 1-4 (3 days). Direct flight. ✅ Good deal - 59% below typical.

ORD → London Heathrow - $399 round-trip with Multiple Airlines. Feb 8-11 (3 days). Direct flight. ✅ Good deal.

ORD → Rome - $399 round-trip with Multiple Airlines. Feb 22-25 (3 days). Direct flight. ✅ Good deal - 51% below typical.

ORD → Barcelona - $403 round-trip with Multiple Airlines. Apr 12-15 (3 days). Direct flight. ✅ Good deal - 37% below typical.

ORD → Lisbon - $412 round-trip with Multiple Airlines. Feb 8-11 (3 days). Direct flight. ✅ Good deal - 24% below typical.

ORD → Madrid - $415 round-trip with Multiple Airlines. Feb 8-11 (3 days). Direct flight. ✅ Good deal - 64% below typical.

ORD → Delhi - $326 round-trip with Multiple Airlines. Feb 16-21 (5 days). Direct flight. ✅ Good deal - 44% below typical.

ORD → Tokyo Narita - $470 round-trip with Multiple Airlines. Apr 6-11 (5 days). Direct flight. ✅ Good deal - 47% below typical. Spring cherry blossoms!

ORD → Tokyo Haneda - $470 round-trip with Multiple Airlines. Apr 6-11 (5 days). Direct flight. ✅ Good deal - 42% below typical.

Midway has the best domestic budget deals this week (Phoenix at $28!), while O'Hare dominates international routes with direct flights to Europe and Asia. For Caribbean escapes, O'Hare offers more direct options and better frequencies.

This week's premium cabin deals are exceptional - we found Business Class to Phoenix for just $133 (72% off!) and Miami Business Class at $135 (61% off). These are prices you'd normally pay for economy!

MDW → Phoenix (Business) - $133 round-trip

Usually $133-$808. Save $675 with flexibility!

Best dates to fly:

ORD → Miami (Business) - $135 round-trip | Usually $135-$549. Save 61%! 20°C beach weather.

ORD → Los Angeles (Business) - $164 round-trip | Usually $164-$487. Save 50%!

ORD → Seattle (Business) - $274 round-trip | Usually $274-$474. Apr 8-13.

ORD → San Francisco (Business) - $388 round-trip | Usually $388-$740. Save $352!

ORD → Cancun (Business) - $191 round-trip | Usually $191-$336. Apr 14-19. 24°C beach paradise.

ORD → Punta Cana (Business) - $228 round-trip | Usually $228-$1,485. Save 73%! Dominican Republic luxury.

ORD → San Juan (Business) - $413 round-trip | Usually $413-$824. Feb 23-28.

ORD → Montego Bay (Business) - $430 round-trip | Usually $430-$1,405. Save 53%! Jamaica sunshine at 27°C.

ORD → Rome (Business) - $2,644 round-trip | Usually $2,644-$6,234. Save 40%! Mar 24-27.

ORD → Lisbon (Business) - $2,929 round-trip | Usually $2,929-$3,805. Feb 8-11 weekend escape.

ORD → Paris (Business) - $3,017 round-trip | Usually $3,017-$3,942. Apr 29-May 2.

ORD → Amsterdam (Business) - $3,066 round-trip | Usually $3,066-$3,766. Apr 29-May 2.

ORD → Dublin (Business) - $3,449 round-trip | Usually $3,449-$13,134. Save 58%! Incredible value.

ORD → Delhi (Business) - $3,152 round-trip | Usually $3,152-$6,852. Save 37%! Feb 18-23.

ORD → Tokyo Narita (Business) - $3,134 round-trip | Usually $3,134-$5,074. Apr 23-28. Cherry blossom season!

ORD → Tokyo Haneda (Business) - $3,134 round-trip | Usually $3,134-$4,034. Apr 23-28. More convenient airport!

ORD → Seoul (Business) - $3,431 round-trip | Usually $3,431-$4,744. Feb 12-17 (President's Day week!).

ORD → Dubai (Business) - $4,418 round-trip | Usually $4,418-$11,846. Save 46%! Feb 16-21. 19°C desert luxury.

ORD → Tel Aviv (Business) - $4,484 round-trip | Usually $4,484-$6,734. Feb 12-17.

O'Hare vs Midway for Premium Travel:

Premium Economy options available for most European and Asian routes. Typically priced 30-50% above economy with significantly more comfort. Best value on flights over 7 hours.

All deals are subject to availability and may change. Prices shown are for round-trip travel unless otherwise noted. Premium members get deal alerts 24 hours before public release.