Skip to content
Sign in

Cheap flights from Miami to Chicago

Recently found return fares from $99, with November the cheapest month we know of. Compare dates, then book with the partner you choose.

Cheapest months to fly

Lowest recently found return fare in each month. Tap a month to see that month's calendar.

$183 Oct2026 $99 Nov2026 $152 Dec2026 $99 Jan2027 $275 Jun2027

Miami → Chicago

November 2026

Mon Tue Wed Thu Fri Sat Sun 1 $131 2 $120 3 $106 4 5 6 7 8 9 10 11 12 13 14 $59 15 $164 16 17 18 $100 19 20 21 22 23 $83 24 25 26 27 28 29 30
LowerHigherLowest this month

Lowest fares for the best day

  • JetBlueWed 11 Nov – Sun 15 Nov · Direct · 3h 27m $163
  • JetBlueWed 11 Nov – Mon 16 Nov · Direct · 3h 21m $197
See all flights for these dates

Airports in Chicago

  • ORDO'Hare
  • MDWMidway

Airport in Miami

  • MIAMiami International

Watch this route

MIA
CHI

We'll ask you to confirm your email. Sign in to manage all alerts in one place.

More trips from Miami

All flights from Miami Chicago to Miami flights
SJUfrom $103 Atlantafrom $127 Dallasfrom $145 BWIfrom $169 SDQfrom $199 CMHfrom $237 New Yorkfrom $238 Washingtonfrom $255

FAQ

Questions about this route

Still have a question?

Search the help center or send us a message. We reply by email.

Help center Contact us
01What is the cheapest month to fly from Miami to Chicago?

Based on recently found fares, November 2026 has the lowest price we know of, from $99. Prices change often, so check the calendar for current fares.

02Which airports serve Chicago?

Chicago is served by O'Hare (ORD), Midway (MDW). Searching the city code compares all of them at once.

03Are the prices on this page final?

No. They are recently found fares. When you open a deal, the partner shows the live price, including taxes and fees, before you pay.

04How can I get an alert when flights to Chicago get cheaper?

Use the price alert on this page. Choose your dates or a whole month and we will email you when the fare drops.