An aerial view of the coastline and high-rise buildings in Miami Beach, Florida
53% below the usual fare
Exit Row · Boarding passSeat 14C

Cheap flights ChicagoMiami

From
CHIChicago
To
MIAMiami
Travel
November 2026
Flight
1 stop, return

Fare from Chicago

US$169

Usually about US$359

-53%vs the usual price

Get the dates and the link

Price seen 29 Oct 2026 · fares change fast and can sell out

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Aerial photography of buildings
Shawn Henley / Unsplash
Palm trees line a sunny street with white buildings
Luise and Nic / Unsplash

Why go

Miami.

Sun, beaches and one of the most Latin American cities outside Latin America.

Best timeNovember to April.

  • Beach
  • Big city
  • Nightlife
  • Food

Three things to do

  1. South Beach and Art Deco
  2. Little Havana's cafes
  3. A day trip to the Everglades
Distance
1,917 km
Flight
1 stop
Trip
Return

Make it a trip.

Also boarding from Chicago.

Every deal from Chicago

Prices are the cheapest fare we found from Chicago, in USD, for one adult, and can change when you click. Some links are affiliate links: they never change which deals we send or what you pay. How we make money.