O'Hare

Chicago to Frankfurt from just $829

Save 36% on a direct flight to Germany this summer - plus unlock Business Class deals and premium routes with a Premium upgrade.

55 flight deals from Chicago (from $28)

This week's best fares from ORD and MDW - save up to 71% on flights to Phoenix, Miami, LA, Europe, Asia and more. Plus: premium Business Class deals unlocked for subscribers.

$40 Chicago to Miami + 52 more deals

This week's best flight deals from O'Hare and Midway - save up to 78% on flights to the Caribbean, Europe, Asia, and more. Premium members get access to Business Class deals from $149.

Chicago Flight Deals - Fly to Miami for Just $40 Round-Trip This April

57 deals from ORD and MDW this week - economy steals from $40, plus Business Class secrets for premium subscribers

Chicago Flight Deals - $28 Round-Trip to Miami from O'Hare (March 5, 2026)

Insane deals this week from ORD and MDW - Miami for $28, Cancun for $119, Tokyo for $545. Plus: premium cabin deals locked inside for subscribers.

Chicago Flight Deals - Fly to Miami for Just $28 Round-Trip This Week

Incredible fares from ORD and MDW - plus Business Class steals and warm escapes unlocked for Premium members

Chicago Flight Deals: Fly to Phoenix for Just $28 Round-Trip This Week

57 deals from ORD & MDW - warm escapes, Europe under $400, and premium cabin deals for subscribers only

Chicago Flight Deals: Miami from $28, Europe from $394

Escape Chicago winter with warm getaways starting at $28. Premium Business Class deals unlocked for subscribers.

Chicago Flight Deals: Miami from $31, Phoenix from $28 + Premium Business Class Steals

Escape the February freeze with these warm getaways. Plus exclusive Business Class deals for Premium members.

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

Escape the Chicago cold with warm getaways starting at $28 round-trip. Premium subscribers unlock luxury Business Class deals from $133.

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

55 handpicked deals from O'Hare & Midway • Warm escapes from $34 • Premium Business Class deals inside

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

Incredible winter escapes starting at $28 round-trip. Plus: Premium cabin deals under $300!

Chicago Flight Deals: San Juan from $46, Europe from $350 | Week of Dec 25

Your weekly roundup: Puerto Rico steals, warm Caribbean escapes, and premium business class bargains from ORD & MDW

Chicago Flight Deals: Cancun from $78, Europe from $154 & More! ✈️

Incredible winter escapes + premium cabin deals starting at $197. Save up to 100% on 34 routes from O'Hare & Midway.