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Cheap flights from Chicago

We are watching 224 routes out of Chicago. The cheapest fare we can vouch for today is €22, and for each one we say whether today is a good moment or you should wait.

See this fare · Fort Lauderdale €22

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Where to fly from Chicago

Chicago → Fort Lauderdale

Frontier Airlines Based on 1644 observations ✈ Direct

Chicago → Baltimore

Frontier Airlines Based on 364 observations ✈ Direct

Chicago → Charlotte

United Airlines Based on 72 observations ✈ Direct

Chicago → Denver

Frontier Airlines Based on 286 observations ✈ Direct

Chicago → Quincy

Contour Airlines Based on 57 observations ✈ Direct

Chicago → Atlanta

Frontier Airlines Based on 550 observations ✈ Direct

Chicago → St Louis

Southwest Airlines Based on 277 observations ✈ Direct

Chicago → Phoenix

Frontier Airlines Based on 257 observations ✈ Direct

Chicago → Memphis

American Airlines Based on 77 observations ✈ Direct

Chicago → Washington

Frontier Airlines Based on 298 observations 1 stop

Chicago → Miami

Frontier Airlines Based on 708 observations 1 stop

Chicago → Minneapolis

Southwest Airlines Based on 465 observations ✈ Direct

Chicago → Indianapolis

American Airlines Based on 122 observations ✈ Direct

Chicago → San Juan

F9 Based on 191 observations ✈ Direct

Chicago → Pittsburgh

American Airlines Based on 135 observations ✈ Direct

Chicago → Columbia

American Airlines Based on 47 observations ✈ Direct

Chicago → Knoxville/Maryville

Allegiant Air Based on 100 observations ✈ Direct

Chicago → Las Vegas

Frontier Airlines Based on 745 observations ✈ Direct

Chicago → Houston

Frontier Airlines Based on 272 observations ✈ Direct

Chicago → Dallas-Fort Worth

Frontier Airlines Based on 381 observations ✈ Direct

Chicago → Tampa

Frontier Airlines Based on 306 observations 1 stop

Chicago → Cincinnati / Covington

Frontier Airlines Based on 86 observations 1 stop

Chicago → San Diego

Frontier Airlines Based on 203 observations 1 stop

Chicago → Nashville

American Airlines Based on 193 observations ✈ Direct

Chicago → Austin

Frontier Airlines Based on 305 observations 1 stop

Chicago → Philadelphia

Frontier Airlines Based on 274 observations ✈ Direct

Chicago → Ontario

Frontier Airlines Based on 454 observations 1 stop

Chicago → San Francisco

Frontier Airlines Based on 395 observations 1 stop

Chicago → Columbus

American Airlines Based on 151 observations ✈ Direct

Chicago → Cedar Rapids

American Airlines Based on 83 observations ✈ Direct

Chicago → Cleveland

American Airlines Based on 186 observations ✈ Direct

Chicago → Rochester

American Airlines Based on 59 observations ✈ Direct

Chicago → Louisville

American Airlines Based on 44 observations ✈ Direct

Chicago → Lexington

American Airlines Based on 30 observations ✈ Direct

Chicago → Raleigh/Durham

Frontier Airlines Based on 90 observations 1 stop

Chicago → Savoy

American Airlines Based on 41 observations ✈ Direct

Chicago → Los Angeles

Frontier Airlines Based on 593 observations 1 stop

Chicago → Des Moines

American Airlines Based on 41 observations ✈ Direct

Chicago → Peoria

American Airlines Based on 66 observations ✈ Direct

Chicago → Bloomington/Normal

American Airlines Based on 12 observations ✈ Direct

Chicago → New York

American Airlines Based on 1065 observations ✈ Direct

Chicago → New Orleans

Frontier Airlines Based on 280 observations 1 stop

Chicago → Boston

jetBlue Based on 483 observations ✈ Direct

Chicago → Buffalo

American Airlines Based on 99 observations ✈ Direct

Chicago → Huntsville

Frontier Airlines Based on 45 observations 1 stop

Chicago → Sioux Falls

American Airlines Based on 34 observations ✈ Direct

Chicago → San Jose

Frontier Airlines Based on 248 observations 1 stop

Chicago → Grand Rapids

American Airlines Based on 51 observations ✈ Direct

Chicago → Dayton

American Airlines Based on 49 observations ✈ Direct

Chicago → Norfolk

Frontier Airlines Based on 26 observations 1 stop

Chicago → Traverse City

American Airlines Based on 36 observations ✈ Direct

Chicago → Seattle

Frontier Airlines Based on 323 observations 1 stop

Chicago → Guadalajara

Viva Aerobus Based on 184 observations ✈ Direct

Chicago → Fort Wayne

American Airlines Based on 22 observations ✈ Direct

Chicago → Chattanooga

United Airlines Based on 12 observations ✈ Direct

Chicago → Muskegon

Denver Air Connection (DAC) Based on 32 observations ✈ Direct

Chicago → Long Beach

Alaska Airlines Based on 157 observations 1 stop

Chicago → Vancouver

Frontier Airlines Based on 66 observations 1 stop

Chicago → Sarasota/Bradenton

Frontier Airlines Based on 38 observations 2 stops

Chicago → Jacksonville

Frontier Airlines Based on 183 observations 1 stop

Booking tips from our fare data

How far in advance should you book a flight?: Book 1–1.5 months before departure. Tracking the same flights at every lead time (94,914 flights on 19,442 routes, 2026-06-14 to 2026-11-04), that window had the smallest average premium over each flight's lowest fare: +16.8%, against +49.3% in the last 3 days.
What is the cheapest day of the week to fly?: Wednesday. Comparing each fare with the median of its own route, Wednesday departures were +3.4% and Tuesday +4.2%, while Friday was the dearest at +10.6%. Weekend departures cost more than midweek ones.
What is the cheapest month to fly?: November 2026. Comparing each route's fares month by month (booked 8–60 days ahead), November 2026 departures were -1.1% against the route's own median, while January 2027 was the dearest at +17.5%. Covers September 2026, October 2026, November 2026, December 2026, January 2027; fares observed 2026-06-14 to 2026-11-04.

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