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 Quincy at $82.

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: October 13, 2026 at 8:00 AM UTC

Current Deals from Chicago

Live deals curated from the latest Chicago search snapshot.

20 routes
$82

Chicago ↔ Quincy

Current price $82
Historical low $82
$319

Chicago ↔ Milwaukee

Current price $319
Historical low $295
$423

Chicago ↔ Bogotá

Current price $423
Historical low $383
$434

Chicago ↔ Cartagena

Current price $434
Historical low $398
$465

Chicago ↔ Reykjavik

Current price $465
Historical low $396
$490

Chicago ↔ Copenhagen

Current price $490
Historical low $485
$684

Chicago ↔ Casablanca

Current price $684
Historical low $681
$695

Chicago ↔ Cairo

Current price $695
Historical low $642
$710

Chicago ↔ Dublin

Current price $710
Historical low $499
$720

Chicago ↔ Mumbai

Current price $720
Historical low $669
$750

Chicago ↔ Istanbul

Current price $750
Historical low $750
$759

Chicago ↔ Medina

Current price $759
Historical low $729
$771

Chicago ↔ Dubai

Current price $771
Historical low $699
$881

Chicago ↔ Abu Dhabi

Current price $881
Historical low $858
$1096

Chicago ↔ Auckland

Current price $1096
Historical low $1092
$1300

Chicago ↔ Melbourne

Current price $1300
Historical low $1262
$1346

Chicago ↔ Brisbane

Current price $1346
Historical low $1289
$1498

Chicago ↔ Nadi

Current price $1498
Historical low $1152
$1618

Chicago ↔ Tahiti

Current price $1618
Historical low $936
$1732

Chicago ↔ Sydney

Current price $1732
Historical low $1239

Best Historical Deals from Chicago

Lowest recorded fares for Chicago routes in Roam Travel history.

80 routes
$43

Chicago ↔ Atlanta

Cheapest ever found $43
$48

Chicago ↔ Philadelphia

Cheapest ever found $48
$49

Chicago ↔ Fort Lauderdale

Cheapest ever found $49
$53

Chicago ↔ London

Cheapest ever found $53
$56

Chicago ↔ Orlando

Cheapest ever found $56
$64

Chicago ↔ Washington, D.C.

Cheapest ever found $64
$65

Chicago ↔ Denver

Cheapest ever found $65
$74

Chicago ↔ Knoxville

Cheapest ever found $74
$82

Chicago ↔ Destin

Cheapest ever found $82
$83

Chicago ↔ Orlando

Cheapest ever found $83
$84

Chicago ↔ Puebla

Cheapest ever found $84
$87

Chicago ↔ Tampa

Cheapest ever found $87
$117

Chicago ↔ Cleveland

Cheapest ever found $117
$117

Chicago ↔ Minneapolis

Cheapest ever found $117
$136

Chicago ↔ Los Angeles

Cheapest ever found $136
$158

Chicago ↔ Decatur

Cheapest ever found $158
$190

Chicago ↔ Toronto

Cheapest ever found $190
$195

Chicago ↔ New York

Cheapest ever found $195
$210

Chicago ↔ Boston

Cheapest ever found $210
$243

Chicago ↔ Miami

Cheapest ever found $243
$278

Chicago ↔ New York

Cheapest ever found $278
$281

Chicago ↔ Punta Cana

Cheapest ever found $281
$350

Chicago ↔ Toronto

Cheapest ever found $350
$361

Chicago ↔ Montreal

Cheapest ever found $361
$374

Chicago ↔ Luxembourg

Cheapest ever found $374
$375

Chicago ↔ Gothenburg

Cheapest ever found $375
$376

Chicago ↔ Stockholm

Cheapest ever found $376
$379

Chicago ↔ Peoria

Cheapest ever found $379
$402

Chicago ↔ Barcelona

Cheapest ever found $402
$405

Chicago ↔ Brussels

Cheapest ever found $405
$426

Chicago ↔ Santo Domingo

Cheapest ever found $426
$426

Chicago ↔ Cali

Cheapest ever found $426
$431

Chicago ↔ Cúcuta

Cheapest ever found $431
$440

Chicago ↔ Bucaramanga

Cheapest ever found $440
$440

Chicago ↔ Gdańsk

Cheapest ever found $440
$443

Chicago ↔ Medellín

Cheapest ever found $443
$457

Chicago ↔ Oslo

Cheapest ever found $457
$465

Chicago ↔ Stavanger

Cheapest ever found $465
$466

Chicago ↔ Oslo

Cheapest ever found $466
$480

Chicago ↔ Guayaquil

Cheapest ever found $480
$481

Chicago ↔ Amsterdam

Cheapest ever found $481
$481

Chicago ↔ Barranquilla

Cheapest ever found $481
$495

Chicago ↔ Bergen

Cheapest ever found $495
$504

Chicago ↔ Paris

Cheapest ever found $504
$506

Chicago ↔ Quito

Cheapest ever found $506
$514

Chicago ↔ São Paulo

Cheapest ever found $514
$525

Chicago ↔ Madrid

Cheapest ever found $525
$554

Chicago ↔ Armenia

Cheapest ever found $554
$558

Chicago ↔ Porto

Cheapest ever found $558
$594

Chicago ↔ Tromsø

Cheapest ever found $594
$623

Chicago ↔ Prague

Cheapest ever found $623
$640

Chicago ↔ Lisbon

Cheapest ever found $640
$664

Chicago ↔ Glasgow

Cheapest ever found $664
$676

Chicago ↔ Warsaw

Cheapest ever found $676
$696

Chicago ↔ New Delhi

Cheapest ever found $696
$718

Chicago ↔ Bengaluru

Cheapest ever found $718
$740

Chicago ↔ Kochi

Cheapest ever found $740
$747

Chicago ↔ Islamabad

Cheapest ever found $747
$748

Chicago ↔ Algiers

Cheapest ever found $748
$748

Chicago ↔ Yerevan

Cheapest ever found $748
$757

Chicago ↔ Caracas

Cheapest ever found $757
$765

Chicago ↔ Hyderabad

Cheapest ever found $765
$768

Chicago ↔ Beirut

Cheapest ever found $768
$769

Chicago ↔ Riyadh

Cheapest ever found $769
$770

Chicago ↔ Doha

Cheapest ever found $770
$771

Chicago ↔ Jeddah

Cheapest ever found $771
$773

Chicago ↔ Fortaleza

Cheapest ever found $773
$777

Chicago ↔ Dammam

Cheapest ever found $777
$804

Chicago ↔ Recife

Cheapest ever found $804
$805

Chicago ↔ Istanbul

Cheapest ever found $805
$815

Chicago ↔ Santiago de Chile

Cheapest ever found $815
$847

Chicago ↔ Manila

Cheapest ever found $847
$879

Chicago ↔ Baku

Cheapest ever found $879
$919

Chicago ↔ Amman

Cheapest ever found $919
$1039

Chicago ↔ Tel Aviv

Cheapest ever found $1039
$1271

Chicago ↔ Hagåtña

Cheapest ever found $1271
$1318

Chicago ↔ Christchurch

Cheapest ever found $1318
$1354

Chicago ↔ Saipan

Cheapest ever found $1354
$1354

Chicago ↔ Perth

Cheapest ever found $1354
$1492

Chicago ↔ Adelaide

Cheapest ever found $1492

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.

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

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