Flights from Chicago to Brainerd

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.

Tue, Sep 23 - Tue, Sep 30

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$97 Roundtrip, found 4 days ago

$97

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Sep 23 from Midway Intl. to Minneapolis - St. Paul Intl., returning Tue, Sep 30, priced at $97 found 4 days ago

Tue, Sep 23 - Sun, Sep 28

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$110 Roundtrip, found 4 days ago

$110

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Sep 23 from Midway Intl. to Minneapolis - St. Paul Intl., returning Sun, Sep 28, priced at $110 found 4 days ago

Tue, Sep 23 - Wed, Oct 1

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$147 Roundtrip, found 4 days ago

$147

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Sep 23 from Midway Intl. to Minneapolis - St. Paul Intl., returning Wed, Oct 1, priced at $147 found 4 days ago

Thu, Sep 25 - Sun, Sep 28

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$160 Roundtrip, found 4 days ago

$160

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Sep 25 from Midway Intl. to Minneapolis - St. Paul Intl., returning Sun, Sep 28, priced at $160 found 4 days ago

Fri, Sep 26 - Sun, Sep 28

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$166 Roundtrip, found 4 days ago

$166

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Fri, Sep 26 from Midway Intl. to Minneapolis - St. Paul Intl., returning Sun, Sep 28, priced at $166 found 4 days ago

Tue, Sep 23 - Thu, Sep 25

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$167 Roundtrip, found 4 days ago

$167

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Sep 23 from Midway Intl. to Minneapolis - St. Paul Intl., returning Thu, Sep 25, priced at $167 found 4 days ago

Tue, Sep 23 - Mon, Oct 6

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$188 Roundtrip, found 4 days ago

$188

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Sep 23 from Midway Intl. to Minneapolis - St. Paul Intl., returning Mon, Oct 6, priced at $188 found 4 days ago

Tue, Sep 23 - Thu, Oct 2

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$197 Roundtrip, found 4 days ago

$197

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Sep 23 from Midway Intl. to Minneapolis - St. Paul Intl., returning Thu, Oct 2, priced at $197 found 4 days ago

Fri, Sep 26 - Sun, Sep 28

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$204 Roundtrip, found 4 days ago

$204

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Fri, Sep 26 from Midway Intl. to Minneapolis - St. Paul Intl., returning Sun, Sep 28, priced at $204 found 4 days ago

Mon, Sep 29 - Mon, Oct 6

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$208 Roundtrip, found 4 days ago

$208

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Mon, Sep 29 from Midway Intl. to Minneapolis - St. Paul Intl., returning Mon, Oct 6, priced at $208 found 4 days ago

Fri, Sep 26 - Sun, Sep 28

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$210 Roundtrip, found 4 days ago

$210

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Sep 26 from Midway Intl. to Minneapolis - St. Paul Intl., returning Sun, Sep 28, priced at $210 found 4 days ago

Fri, Sep 26 - Wed, Oct 1

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$247 Roundtrip, found 4 days ago

$247

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Sep 26 from Midway Intl. to Minneapolis - St. Paul Intl., returning Wed, Oct 1, priced at $247 found 4 days ago

Fri, Sep 26 - Sun, Sep 28

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$259 Roundtrip, found 4 days ago

$259

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Sep 26 from Midway Intl. to Minneapolis - St. Paul Intl., returning Sun, Sep 28, priced at $259 found 4 days ago

Fri, Sep 26 - Sun, Sep 28

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$270 Roundtrip, found 4 days ago

$270

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Sep 26 from Midway Intl. to Minneapolis - St. Paul Intl., returning Sun, Sep 28, priced at $270 found 4 days ago

Fri, Sep 26 - Sun, Sep 28

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$284 Roundtrip, found 4 days ago

$284

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Fri, Sep 26 from Midway Intl. to Minneapolis - St. Paul Intl., returning Sun, Sep 28, priced at $284 found 4 days ago

Fri, Sep 26 - Sun, Sep 28

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$289 Roundtrip, found 4 days ago

$289

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Sep 26 from Midway Intl. to Minneapolis - St. Paul Intl., returning Sun, Sep 28, priced at $289 found 4 days ago

Fri, Sep 26 - Sun, Sep 28

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$297 Roundtrip, found 4 days ago

$297

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Sep 26 from Midway Intl. to Minneapolis - St. Paul Intl., returning Sun, Sep 28, priced at $297 found 4 days ago

Fri, Sep 26 - Sun, Sep 28

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$318 Roundtrip, found 4 days ago

$318

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Sep 26 from Midway Intl. to Minneapolis - St. Paul Intl., returning Sun, Sep 28, priced at $318 found 4 days ago

Fri, Sep 26 - Sun, Sep 28

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$337 Roundtrip, found 4 days ago

$337

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Sep 26 from Midway Intl. to Minneapolis - St. Paul Intl., returning Sun, Sep 28, priced at $337 found 4 days ago

Fri, Sep 26 - Sun, Sep 28

MDW

Midway Intl.

MSP

Minneapolis - St. Paul Intl.

$357 Roundtrip, found 4 days ago

$357

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Sep 26 from Midway Intl. to Minneapolis - St. Paul Intl., returning Sun, Sep 28, priced at $357 found 4 days ago