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 Destin at $105.
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: September 2, 2026 at 8:00 AM UTC
Live deals curated from the latest Chicago search snapshot.
$105
$115
$117
$287
$291
$362
$409
$447
$466
$693
$696
$697
$698
$708
$772
$775
$809
$858
$925
$925
$1023
$1088
$1307
$1369
$1422
$1653
$1694
$1694
$2260
$2274
$12023
$12024
$12279
Lowest recorded fares for Chicago routes in Roam Travel history.
$54
$54
$56
$65
$75
$78
$83
$88
$91
$105
$117
$131
$159
$190
$309
$309
$319
$332
$334
$363
$375
$376
$380
$385
$394
$421
$432
$451
$456
$472
$499
$512
$525
$549
$611
$613
$624
$667
$674
$681
$694
$700
$718
$758
$761
$770
$777
$778
$797
$798
$818
$864
$888
$898
$916
$969
$1150
$1492
$2278
$3173
$3325
$3430
$3430
$11698
Details about how these city landing prices are generated.
Browse current and historical flight deals departing from other major cities.