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 Knoxville at $103.
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 6, 2026 at 5:10 PM UTC
Live deals curated from the latest Chicago search snapshot.
$103
$105
$159
$319
$373
$395
$406
$407
$657
$684
$688
$689
$691
$702
$759
$781
$809
$858
$870
$926
$968
$971
$979
$1330
$1440
$1534
$1684
$1693
$2275
$2635
$3052
$3140
Lowest recorded fares for Chicago routes in Roam Travel history.
$49
$53
$54
$54
$56
$65
$75
$83
$88
$91
$97
$105
$117
$131
$190
$309
$309
$319
$332
$334
$363
$375
$376
$379
$380
$385
$394
$421
$432
$449
$451
$456
$472
$476
$512
$525
$534
$549
$613
$624
$626
$667
$681
$694
$700
$718
$761
$770
$777
$778
$797
$798
$818
$845
$864
$888
$898
$916
$1150
$1492
$2079
$2081
$2237
$2278
$3173
$3430
$11698
$11901
Details about how these city landing prices are generated.
Browse current and historical flight deals departing from other major cities.