Flights from Chicago to Fleming Island

Cheapest flights from Chicago

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Oct 15 - Sat, Oct 18

MDW

Midway Intl.

JAX

Jacksonville Intl.

$201 Roundtrip, found 17 hours ago

$201

Roundtrip

found 17 hours ago

Select Delta flight, departing Wed, Oct 15 from Midway Intl. to Jacksonville Intl., returning Sat, Oct 18, priced at $201 found 17 hours ago

Thu, Oct 16 - Thu, Oct 23

MDW

Midway Intl.

JAX

Jacksonville Intl.

$251 Roundtrip, found 17 hours ago

$251

Roundtrip

found 17 hours ago

Select Frontier Airlines flight, departing Thu, Oct 16 from Midway Intl. to Jacksonville Intl., returning Thu, Oct 23, priced at $251 found 17 hours ago

Wed, Oct 15 - Fri, Oct 17

MDW

Midway Intl.

JAX

Jacksonville Intl.

$270 Roundtrip, found 17 hours ago

$270

Roundtrip

found 17 hours ago

Select Delta flight, departing Wed, Oct 15 from Midway Intl. to Jacksonville Intl., returning Fri, Oct 17, priced at $270 found 17 hours ago

Fri, Oct 17 - Thu, Oct 23

MDW

Midway Intl.

JAX

Jacksonville Intl.

$272 Roundtrip, found 17 hours ago

$272

Roundtrip

found 17 hours ago

Select Frontier Airlines flight, departing Fri, Oct 17 from Midway Intl. to Jacksonville Intl., returning Thu, Oct 23, priced at $272 found 17 hours ago

Thu, Oct 16 - Mon, Oct 20

MDW

Midway Intl.

JAX

Jacksonville Intl.

$277 Roundtrip, found 17 hours ago

$277

Roundtrip

found 17 hours ago

Select Frontier Airlines flight, departing Thu, Oct 16 from Midway Intl. to Jacksonville Intl., returning Mon, Oct 20, priced at $277 found 17 hours ago

Thu, Oct 16 - Sat, Oct 18

MDW

Midway Intl.

JAX

Jacksonville Intl.

$283 Roundtrip, found 17 hours ago

$283

Roundtrip

found 17 hours ago

Select Delta flight, departing Thu, Oct 16 from Midway Intl. to Jacksonville Intl., returning Sat, Oct 18, priced at $283 found 17 hours ago

Wed, Oct 15 - Sun, Oct 19

MDW

Midway Intl.

JAX

Jacksonville Intl.

$289 Roundtrip, found 17 hours ago

$289

Roundtrip

found 17 hours ago

Select Delta flight, departing Wed, Oct 15 from Midway Intl. to Jacksonville Intl., returning Sun, Oct 19, priced at $289 found 17 hours ago

Fri, Oct 17 - Mon, Oct 20

MDW

Midway Intl.

JAX

Jacksonville Intl.

$298 Roundtrip, found 17 hours ago

$298

Roundtrip

found 17 hours ago

Select Frontier Airlines flight, departing Fri, Oct 17 from Midway Intl. to Jacksonville Intl., returning Mon, Oct 20, priced at $298 found 17 hours ago

Thu, Oct 16 - Sun, Oct 19

MDW

Midway Intl.

JAX

Jacksonville Intl.

$299 Roundtrip, found 17 hours ago

$299

Roundtrip

found 17 hours ago

Select Frontier Airlines flight, departing Thu, Oct 16 from Midway Intl. to Jacksonville Intl., returning Sun, Oct 19, priced at $299 found 17 hours ago

Thu, Oct 16 - Fri, Oct 17

MDW

Midway Intl.

JAX

Jacksonville Intl.

$306 Roundtrip, found 17 hours ago

$306

Roundtrip

found 17 hours ago

Select Frontier Airlines flight, departing Thu, Oct 16 from Midway Intl. to Jacksonville Intl., returning Fri, Oct 17, priced at $306 found 17 hours ago

Thu, Oct 16 - Mon, Oct 20

MDW

Midway Intl.

JAX

Jacksonville Intl.

$316 Roundtrip, found 17 hours ago

$316

Roundtrip

found 17 hours ago

Select Frontier Airlines flight, departing Thu, Oct 16 from Midway Intl. to Jacksonville Intl., returning Mon, Oct 20, priced at $316 found 17 hours ago

Fri, Oct 17 - Sat, Oct 18

MDW

Midway Intl.

JAX

Jacksonville Intl.

$330 Roundtrip, found 17 hours ago

$330

Roundtrip

found 17 hours ago

Select Delta flight, departing Fri, Oct 17 from Midway Intl. to Jacksonville Intl., returning Sat, Oct 18, priced at $330 found 17 hours ago

Thu, Oct 16 - Mon, Oct 20

MDW

Midway Intl.

JAX

Jacksonville Intl.

$356 Roundtrip, found 17 hours ago

$356

Roundtrip

found 17 hours ago

Select Frontier Airlines flight, departing Thu, Oct 16 from Midway Intl. to Jacksonville Intl., returning Mon, Oct 20, priced at $356 found 17 hours ago

Thu, Oct 16 - Mon, Oct 20

MDW

Midway Intl.

JAX

Jacksonville Intl.

$357 Roundtrip, found 17 hours ago

$357

Roundtrip

found 17 hours ago

Select Delta flight, departing Thu, Oct 16 from Midway Intl. to Jacksonville Intl., returning Mon, Oct 20, priced at $357 found 17 hours ago

Tue, Oct 14 - Sun, Oct 19

MDW

Midway Intl.

JAX

Jacksonville Intl.

$358 Roundtrip, found 17 hours ago

$358

Roundtrip

found 17 hours ago

Select Delta flight, departing Tue, Oct 14 from Midway Intl. to Jacksonville Intl., returning Sun, Oct 19, priced at $358 found 17 hours ago

Tue, Oct 14 - Mon, Oct 20

MDW

Midway Intl.

JAX

Jacksonville Intl.

$359 Roundtrip, found 17 hours ago

$359

Roundtrip

found 17 hours ago

Select Delta flight, departing Tue, Oct 14 from Midway Intl. to Jacksonville Intl., returning Mon, Oct 20, priced at $359 found 17 hours ago

Thu, Oct 16 - Mon, Oct 20

MDW

Midway Intl.

JAX

Jacksonville Intl.

$392 Roundtrip, found 17 hours ago

$392

Roundtrip

found 17 hours ago

Select Delta flight, departing Thu, Oct 16 from Midway Intl. to Jacksonville Intl., returning Mon, Oct 20, priced at $392 found 17 hours ago

Tue, Oct 14 - Fri, Oct 17

MDW

Midway Intl.

JAX

Jacksonville Intl.

$398 Roundtrip, found 17 hours ago

$398

Roundtrip

found 17 hours ago

Select Delta flight, departing Tue, Oct 14 from Midway Intl. to Jacksonville Intl., returning Fri, Oct 17, priced at $398 found 17 hours ago

Sun, Oct 19 - Wed, Oct 22

MDW

Midway Intl.

JAX

Jacksonville Intl.

$413 Roundtrip, found 17 hours ago

$413

Roundtrip

found 17 hours ago

Select Delta flight, departing Sun, Oct 19 from Midway Intl. to Jacksonville Intl., returning Wed, Oct 22, priced at $413 found 17 hours ago

Thu, Oct 16 - Mon, Oct 20

MDW

Midway Intl.

JAX

Jacksonville Intl.

$427 Roundtrip, found 17 hours ago

$427

Roundtrip

found 17 hours ago

Select Delta flight, departing Thu, Oct 16 from Midway Intl. to Jacksonville Intl., returning Mon, Oct 20, priced at $427 found 17 hours ago