City Flight Deals
Explore current fares and standout historical prices for routes departing from Chicago (ORD, MDW).
The cheapest current fare in this snapshot is Chicago to Washington, D.C. at $69.
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: August 22, 2026 at 8:00 AM UTC
Live deals curated from the latest Chicago search snapshot.
$69
$78
$96
$249
$398
$404
$413
$440
$463
$690
$709
$729
$733
$765
$766
$859
$866
$926
$1003
$1032
$1112
$1309
$1328
$1443
$1702
$1736
$1906
$2195
$3432
$11980
$12023
$12023
$17264
Lowest recorded fares for Chicago routes in Roam Travel history.
$53
$54
$56
$65
$75
$78
$81
$83
$88
$97
$105
$117
$131
$159
$190
$309
$309
$319
$332
$363
$375
$376
$380
$385
$394
$421
$432
$449
$451
$456
$472
$501
$512
$549
$646
$667
$674
$681
$694
$700
$719
$741
$761
$770
$777
$778
$798
$810
$885
$888
$898
$916
$1150
$1492
$2097
$2278
$3173
$3645
$11901
Details about how these city landing prices are generated.
Browse current and historical flight deals departing from other major cities.