Chicago Flight Deals: Phoenix from $28, Warm Escapes & Europe

Your weekly roundup of the best flight deals from Chicago's O'Hare and Midway airports. This week features an unbeatable Phoenix deal, warm Caribbean escapes to beat the winter cold, and surprising Europe fares under $400.

Escape the Chicago cold with these warm getaways:

ORD → Miami - $36 round-trip

20°C average. Beach weather without the flight time. Direct flights, Feb 16-21.

ORD → Cancun - $93 round-trip

24°C average. Beach paradise with warm Caribbean waters. Direct flights, Apr 7-12.

ORD → Punta Cana - $94 round-trip

26°C average. Dominican Republic beach resorts. Direct flights, Mar 9-14.

ORD → Montego Bay - $180 round-trip

27°C average. Jamaica sunshine and reggae vibes. Direct flights, Feb 9-14.

MDW → Phoenix - $28 round-trip with Multiple Airlines. Feb 16-21. Direct. ✅ Good Deal (76% below typical)

Best dates to fly:

ORD → Los Angeles - $64 round-trip with Multiple Airlines. Mar 17-22. Direct. ✅ Good Deal (48% below typical)

MDW → Las Vegas - $80 round-trip with Multiple Airlines. Feb 23-28. Direct. ✅ Good Deal (53% below typical)

ORD → Seattle - $89 round-trip with Multiple Airlines. Feb 5-10. Direct. ✅ Good Deal (36% below typical)

ORD → San Francisco - $129 round-trip with Multiple Airlines. Mar 10-15. Direct. ✅ Good Deal (21% below typical)

ORD → San Juan - $70 round-trip with Multiple Airlines. Feb 3-8. Direct. ✅ Good Deal (60% below typical)

ORD → Cancun - $93 round-trip with Multiple Airlines. Apr 7-12. Direct. ✅ Good Deal (47% below typical)

ORD → Punta Cana - $94 round-trip with Multiple Airlines. Mar 9-14. Direct. ✅ Good Deal (80% below typical)

ORD → Montego Bay - $180 round-trip with Multiple Airlines. Feb 9-14. Direct. ✅ Good Deal (58% below typical)

ORD → London Heathrow - $375 round-trip with Multiple Airlines. Jan 25-28. Direct. ✅ Good Deal (9% below typical)

ORD → Paris - $375 round-trip with Multiple Airlines. Jan 25-28. Direct. ✅ Good Deal (8% below typical)

ORD → Dublin - $375 round-trip with Multiple Airlines. Jan 25-28. Direct. ✅ Good Deal (9% below typical)

ORD → Barcelona - $375 round-trip with Multiple Airlines. Apr 15-18. Direct. ✅ Good Deal (34% below typical)

ORD → Madrid - $375 round-trip with Multiple Airlines. Jan 25-28. Direct. ✅ Good Deal (51% below typical)

ORD → Rome - $395 round-trip with Multiple Airlines. Feb 22-25. Direct. ✅ Good Deal (57% below typical)

ORD → Amsterdam - $395 round-trip with Multiple Airlines. Feb 14-17. Direct. ✅ Good Deal (41% below typical)

ORD → Lisbon - $412 round-trip with Multiple Airlines. Jan 25-28. Direct. ✅ Good Deal (2% below typical)

ORD → Delhi - $316 round-trip with Multiple Airlines. Feb 9-14. Direct. ✅ Good Deal (34% below typical)

ORD → Tokyo Narita - $544 round-trip with Multiple Airlines. Feb 8-13. Direct. ✅ Good Deal (30% below typical)

ORD → Tokyo Haneda - $544 round-trip with Multiple Airlines. Feb 8-13. Direct. ✅ Good Deal (10% below typical)

ORD → Hong Kong - $597 round-trip with Multiple Airlines. Jan 29 - Feb 3. Direct. ✅ Good Deal (12% below typical)

Looking for the best warm-weather deals? O'Hare offers more Caribbean and international connections, while Midway can have surprisingly cheap Southwest fares to Phoenix and Las Vegas. This week's standout $28 Phoenix deal from Midway is a perfect example!

Exclusive for Premium Members: Fly in comfort without the premium price tag.

ORD → Seattle - $274 Business Class round-trip

Feb 5-10. Direct flights. Save $200 vs. typical business fares ($474). 27% below usual pricing.

Best dates to fly:

ORD → Miami - $329 Business Class round-trip

Feb 15-20. Direct flights. 20°C beach weather. Save $433 vs. typical ($762). Perfect winter escape in style!

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

Feb 9-14. Direct flights. Save $680 vs. typical ($1068). 47% below usual pricing.

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

Feb 7-12. Direct flights. Save $260 vs. typical ($664).

ORD → Cancun - $323 Business Class round-trip

Feb 17-22. Direct flights. 24°C Caribbean paradise. Save $660 vs. typical ($983). 51% below usual pricing!

ORD → San Juan - $423 Business Class round-trip

Feb 9-14. Direct flights. Save $544 vs. typical ($967).

ORD → Montego Bay - $461 Business Class round-trip

Apr 19-24. Direct flights. 27°C Jamaica sunshine. Save $305 vs. typical ($766).

ORD → Punta Cana - $536 Business Class round-trip

Mar 8-13. Direct flights. 26°C Dominican Republic beaches. Save $959 vs. typical ($1495). 47% below usual!

ORD → Rome - $2,619 Business Class round-trip

Mar 10-13. Direct flights. Incredible deal: Save $10,740 vs. typical ($13,359). 67% below usual pricing!

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

Jan 23-26. Direct flights. Quick weekend to Portugal.

ORD → Paris - $2,992 Business Class round-trip

Apr 15-18. Direct flights. Save $825 vs. typical ($3,817).

ORD → Amsterdam - $3,041 Business Class round-trip

Apr 15-18. Direct flights. Save $700 vs. typical ($3,741).

ORD → Dublin - $3,424 Business Class round-trip

Feb 17-20. Direct flights. Presidents' Day weekend. Save $4,905 vs. typical ($8,329). 42% below usual!

ORD → Delhi - $3,102 Business Class round-trip

Feb 2-7. Direct flights. Save $3,700 vs. typical ($6,802). 37% below usual pricing!

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

Apr 23-28. Direct flights. Save $900 vs. typical ($4,034).

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

Jan 29 - Feb 3. Direct flights. Save $325 vs. typical ($3,756).

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

Jan 29 - Feb 3. Direct flights. Save $1,112 vs. typical ($5,300).

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

Feb 15-20. Direct flights. 19°C desert luxury. Save $7,428 vs. typical ($11,846). 46% below usual pricing!

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

Jan 29 - Feb 3. Direct flights. Save $10,200 vs. typical ($14,659). 53% below usual!

O'Hare (ORD) - Best for: International flights, business class, premium carriers, one-stop connections to anywhere. Direct flights to Europe, Asia, Middle East, and major US cities. United hub with extensive Star Alliance network.

Midway (MDW) - Best for: Southwest flights, quick domestic getaways, budget travel. Smaller, easier to navigate. Great for Phoenix, Las Vegas, Denver, and Florida. This week's $28 Phoenix deal proves Midway can deliver incredible value!