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 Houston at $88.

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: July 19, 2026 at 8:00 AM UTC

Current Deals from Chicago

Live deals curated from the latest Chicago search snapshot.

35 routes
$88

Chicago ↔ Houston

Current price $88
Historical low $88
$96

Chicago ↔ Destin

Current price $96
Historical low $82
$99

Chicago ↔ Knoxville

Current price $99
Historical low $92
$105

Chicago ↔ Manistee

Current price $105
Historical low $105
$105

Chicago ↔ Burlington

Current price $105
Historical low $105
$105

Chicago ↔ Quincy

Current price $105
Historical low $105
$159

Chicago ↔ Decatur

Current price $159
Historical low $159
$260

Chicago ↔ Milwaukee

Current price $260
Historical low $260
$309

Chicago ↔ South Bend

Current price $309
Historical low $309
$371

Chicago ↔ Reykjavik

Current price $371
Historical low $371
$388

Chicago ↔ Cartagena

Current price $388
Historical low $377
$396

Chicago ↔ Bogotá

Current price $396
Historical low $394
$422

Chicago ↔ Medellín

Current price $422
Historical low $500
$615

Chicago ↔ Lisbon

Current price $615
Historical low $640
$628

Chicago ↔ Barranquilla

Current price $628
Historical low $620
$688

Chicago ↔ Dublin

Current price $688
Historical low $646
$695

Chicago ↔ Cairo

Current price $695
Historical low $695
$708

Chicago ↔ Abu Dhabi

Current price $708
Historical low $708
$761

Chicago ↔ Marrakesh

Current price $761
Historical low $792
$764

Chicago ↔ Glasgow

Current price $764
Historical low $764
$769

Chicago ↔ Casablanca

Current price $769
Historical low $799
$772

Chicago ↔ Istanbul

Current price $772
Historical low $772
$876

Chicago ↔ Mumbai

Current price $876
Historical low $810
$876

Chicago ↔ Dubai

Current price $876
Historical low $876
$980

Chicago ↔ Nadi

Current price $980
Historical low $980
$1009

Chicago ↔ Antalya

Current price $1009
Historical low $888
$1027

Chicago ↔ Riyadh

Current price $1027
Historical low $1027
$1386

Chicago ↔ Sydney

Current price $1386
Historical low $1384
$1649

Chicago ↔ Brisbane

Current price $1649
Historical low $2184
$1689

Chicago ↔ Tahiti

Current price $1689
Historical low $1648
$2080

Chicago ↔ Melbourne

Current price $2080
Historical low $1549
$2176

Chicago ↔ Adelaide

Current price $2176
Historical low $2176
$11920

Chicago ↔ New York

Current price $11920
Historical low $11920
$12095

Chicago ↔ Montreal

Current price $12095
Historical low $12094
$17125

Chicago ↔ São Paulo

Current price $17125
Historical low $17156

Best Historical Deals from Chicago

Lowest recorded fares for Chicago routes in Roam Travel history.

19 routes
$56

Chicago ↔ Atlanta

Cheapest ever found $56
$56

Chicago ↔ Orlando

Cheapest ever found $56
$56

Chicago ↔ Fort Lauderdale

Cheapest ever found $56
$64

Chicago ↔ Washington, D.C.

Cheapest ever found $64
$65

Chicago ↔ Denver

Cheapest ever found $65
$83

Chicago ↔ Orlando

Cheapest ever found $83
$187

Chicago ↔ Minneapolis

Cheapest ever found $187
$190

Chicago ↔ Toronto

Cheapest ever found $190
$375

Chicago ↔ Gothenburg

Cheapest ever found $375
$376

Chicago ↔ Stockholm

Cheapest ever found $376
$379

Chicago ↔ Toronto

Cheapest ever found $379
$501

Chicago ↔ Quito

Cheapest ever found $501
$525

Chicago ↔ Madrid

Cheapest ever found $525
$566

Chicago ↔ Pereira

Cheapest ever found $566
$700

Chicago ↔ Barcelona

Cheapest ever found $700
$902

Chicago ↔ Tokyo

Cheapest ever found $902
$916

Chicago ↔ Istanbul

Cheapest ever found $916
$2617

Chicago ↔ Perth

Cheapest ever found $2617
$12220

Chicago ↔ Punta Cana

Cheapest ever found $12220

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.

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