City Flight Deals

Cheap Flights from Chicago

Explore current fares and standout historical prices for routes departing from Chicago (ORD, MDW).

The cheapest current fare in this snapshot is Chicago to Atlanta at $56.

Roam compares current fare snapshots with previously recorded lows. Prices come from flight-search data, can change quickly, and final booking happens with the airline or travel agency.

Last updated: May 21, 2026 at 2:23 PM UTC

Current Deals from Chicago

Live deals curated from the latest Chicago search snapshot.

5 routes
$56

Chicago ↔ Atlanta

Current price $56
Historical low $56
$57

Chicago ↔ Orlando

Current price $57
Historical low $56
$83

Chicago ↔ Washington, D.C.

Current price $83
Historical low $83
$190

Chicago ↔ Toronto

Current price $190
Historical low $190
$691

Chicago ↔ Lisbon

Current price $691
Historical low $662

Best Historical Deals from Chicago

Lowest recorded fares for Chicago routes in Roam Travel history.

5 routes
$56

Chicago ↔ Fort Lauderdale

Cheapest ever found $56
$375

Chicago ↔ Gothenburg

Cheapest ever found $375
$376

Chicago ↔ Stockholm

Cheapest ever found $376
$700

Chicago ↔ Barcelona

Cheapest ever found $700
$706

Chicago ↔ Madrid

Cheapest ever found $706

Frequently Asked Questions

Details about how these city landing prices are generated.

Each row shows the current cheapest fare we found for that destination using this page's fixed filters.

Current deals show live fares available now, while historical deals show the lowest prices we've previously recorded for each route.

Cheapest Ever Found is the lowest historical price we have recorded for that route in our flight deal history.

This page is refreshed daily at 4:00 AM Eastern Time and serves that scheduled snapshot throughout the day.

Cheap Flights From Other Cities

Browse current and historical flight deals departing from other major US cities.

Cheap Flights From Atlanta
Cheap Flights From New York City
Cheap Flights From Los Angeles
Cheap Flights From Dallas
Cheap Flights From Houston
Cheap Flights From Washington, DC
Cheap Flights From Miami
Cheap Flights From Philadelphia
Cheap Flights From Phoenix
Cheap Flights From Boston
Cheap Flights From San Francisco
Cheap Flights From Seattle
Cheap Flights From Denver
Cheap Flights From Orlando