Cheap Flights from Chicago
Round trips from Chicago (ORD, MDW) priced well under what they usually cost, found by Deal.ai's AI agents on Google Flights within the last hour, up to 70% under Google's typical fare for the route. Fares change by the hour, so this page lists only what was found this hour, and the agents search Chicago again every hour.
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−70%
FlightsGoogle FlightsTiranë: pastel streets and Skanderbeg Square
Apr 4 – Apr 12 · 2 stops · KLM
$734.00round trip$2,412.00 typical fareDeal score 10.0 · Unreal−64%
FlightsGoogle FlightsDestin: Gulf beaches and golf on a whim
Nov 16 – Nov 22 · Nonstop · Allegiant
$132.00round trip$365.00 typical fareDeal score 9.0 · Unreal−57%
FlightsGoogle FlightsSault Ste. Marie: lakes, lighthouses and casino
Nov 28 – Dec 5 · 1 stop · Delta
$218.00round trip$509.00 typical fareDeal score 9.0 · Unreal−55%
FlightsGoogle FlightsSwap deep dish for Mediterranean ruins and beach days
Nov 13 – Nov 21 · 2 stops
$1,071.00round trip$2,404.00 typical fareDeal score 10.0 · Unreal−52%
FlightsGoogle FlightsTrade deep dish for turquoise water and a fishing rod
Nov 28 – Dec 5 · 1 stop · American
$809.00round trip$1,689.00 typical fareDeal score 10.0 · Unreal−52%
FlightsGoogle FlightsMilan: Duomo views and The Last Supper
Dec 6 – Dec 15 · 1 stop
$800.00round trip$1,660.00 typical fareDeal score 10.0 · Unreal−51%
FlightsGoogle FlightsFly to Caracas for the Andes views and colonial plazas
Jan 14 – Jan 21 · 1 stop · COPA
$995.00round trip$2,051.00 typical fareDeal score 10.0 · Unreal−51%
FlightsGoogle FlightsTrade deep dish for Dutch colonial streets in Suriname
Jan 18 – Jan 24 · 1 stop · COPA
$684.00round trip$1,396.00 typical fareDeal score 10.0 · Unreal−49%
FlightsGoogle FlightsAguadilla: Crash Boat Beach and Puerto Rico sun
Dec 11 – Dec 17 · 1 stop · Frontier
$302.00round trip$593.00 typical fareDeal score 8.7 · Steal−49%
FlightsGoogle FlightsZürich: riverbank strolls in Switzerland
Dec 6 – Dec 15 · 2 stops · Delta
$812.00round trip$1,577.00 typical fareDeal score 9.6 · Unreal−48%
FlightsGoogle FlightsBrussels: waffles, beer and EU grandeur
Dec 6 – Dec 15 · 3 stops · KLM
$819.00round trip$1,577.00 typical fareDeal score 9.5 · Unreal−48%
FlightsGoogle FlightsSoak in the Blue Lagoon after landing in Reykjavík
Dec 6 – Dec 12 · Nonstop · Icelandair
$468.00round trip$899.00 typical fareDeal score 9.0 · Unreal−48%
FlightsGoogle FlightsPonce: preserved old town by the sea
Dec 4 – Dec 10 · 1 stop · Frontier
$390.00round trip$747.00 typical fareDeal score 9.0 · Unreal−47%
FlightsGoogle FlightsBeirut: ruins by day, rooftop nights after
Dec 3 – Dec 12 · 2 stops
$791.00round trip$1,491.00 typical fareDeal score 9.3 · Unreal−45%
FlightsGoogle FlightsTrade deep dish for wide-open Badlands skies
Nov 26 – Dec 4 · 1 stop · United
$373.00round trip$683.00 typical fareDeal score 8.1 · Steal−44%
FlightsGoogle FlightsFly into the heart of Civil War country and cave country
Nov 27 – Dec 4 · Nonstop · American
$234.00round trip$418.00 typical fareDeal score 7.3 · Great deal
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Questions and answers
- How does Deal.ai find flight deals from Chicago?
- Every hour Deal.ai's agents search Google Flights for round trips from Chicago (ORD, MDW) and keep the fares furthest under Google's own typical price for each route, one per destination.
- How often are these fares updated?
- Every hour. A fare is listed only during the hour it was found, since airlines change prices through the day; open one to see its dates and book it on Google Flights.
- Are these round-trip fares?
- Yes: each is a round trip in economy, priced for one adult, with its dates, airline and stops shown on the deal.