Flights from Hartford to Chicago

Cheapest flights from Hartford

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.

Sat, Aug 16 - Sun, Aug 24

BDL

Bradley Intl.

MDW

Midway Intl.

$218 Roundtrip, found 13 hours ago

$218

Roundtrip

found 13 hours ago

Select Frontier Airlines flight, departing Sat, Aug 16 from Bradley Intl. to Midway Intl., returning Sun, Aug 24, priced at $218 found 13 hours ago

Sun, Aug 17 - Sun, Aug 24

BDL

Bradley Intl.

MDW

Midway Intl.

$228 Roundtrip, found 13 hours ago

$228

Roundtrip

found 13 hours ago

Select Frontier Airlines flight, departing Sun, Aug 17 from Bradley Intl. to Midway Intl., returning Sun, Aug 24, priced at $228 found 13 hours ago

Sat, Aug 16 - Mon, Aug 18

BDL

Bradley Intl.

MDW

Midway Intl.

$248 Roundtrip, found 13 hours ago

$248

Roundtrip

found 13 hours ago

Select Frontier Airlines flight, departing Sat, Aug 16 from Bradley Intl. to Midway Intl., returning Mon, Aug 18, priced at $248 found 13 hours ago

Tue, Aug 19 - Wed, Aug 20

BDL

Bradley Intl.

ORD

O'Hare Intl.

$257 Roundtrip, found 13 hours ago

$257

Roundtrip

found 13 hours ago

Select American Airlines flight, departing Tue, Aug 19 from Bradley Intl. to O'Hare Intl., returning Wed, Aug 20, priced at $257 found 13 hours ago

Fri, Aug 1 - Thu, Aug 7

BDL

Bradley Intl.

ORD

O'Hare Intl.

$258 Roundtrip, found 3 days ago

$258

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Fri, Aug 1 from Bradley Intl. to O'Hare Intl., returning Thu, Aug 7, priced at $258 found 3 days ago

Tue, Aug 19 - Sat, Aug 23

BDL

Bradley Intl.

MDW

Midway Intl.

$268 Roundtrip, found 13 hours ago

$268

Roundtrip

found 13 hours ago

Select Delta flight, departing Tue, Aug 19 from Bradley Intl. to Midway Intl., returning Sat, Aug 23, priced at $268 found 13 hours ago

Sun, Aug 17 - Tue, Aug 19

BDL

Bradley Intl.

ORD

O'Hare Intl.

$277 Roundtrip, found 13 hours ago

$277

Roundtrip

found 13 hours ago

Select American Airlines flight, departing Sun, Aug 17 from Bradley Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $277 found 13 hours ago

Wed, Aug 20 - Wed, Aug 20

BDL

Bradley Intl.

ORD

O'Hare Intl.

$287 Roundtrip, found 13 hours ago

$287

Roundtrip

found 13 hours ago

Select United flight, departing Wed, Aug 20 from Bradley Intl. to O'Hare Intl., returning Wed, Aug 20, priced at $287 found 13 hours ago

Tue, Aug 19 - Thu, Aug 21

BDL

Bradley Intl.

ORD

O'Hare Intl.

$289 Roundtrip, found 13 hours ago

$289

Roundtrip

found 13 hours ago

Select American Airlines flight, departing Tue, Aug 19 from Bradley Intl. to O'Hare Intl., returning Thu, Aug 21, priced at $289 found 13 hours ago

Mon, Aug 18 - Thu, Aug 21

BDL

Bradley Intl.

ORD

O'Hare Intl.

$302 Roundtrip, found 13 hours ago

$302

Roundtrip

found 13 hours ago

Select American Airlines flight, departing Mon, Aug 18 from Bradley Intl. to O'Hare Intl., returning Thu, Aug 21, priced at $302 found 13 hours ago

Mon, Aug 18 - Fri, Aug 22

BDL

Bradley Intl.

ORD

O'Hare Intl.

$304 Roundtrip, found 13 hours ago

$304

Roundtrip

found 13 hours ago

Select Spirit Airlines flight, departing Mon, Aug 18 from Bradley Intl. to O'Hare Intl., returning Fri, Aug 22, priced at $304 found 13 hours ago

Sun, Aug 17 - Wed, Aug 20

BDL

Bradley Intl.

ORD

O'Hare Intl.

$307 Roundtrip, found 13 hours ago

$307

Roundtrip

found 13 hours ago

Select American Airlines flight, departing Sun, Aug 17 from Bradley Intl. to O'Hare Intl., returning Wed, Aug 20, priced at $307 found 13 hours ago

Fri, Aug 1 - Sun, Aug 3

BDL

Bradley Intl.

ORD

O'Hare Intl.

$308 Roundtrip, found 3 days ago

$308

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Fri, Aug 1 from Bradley Intl. to O'Hare Intl., returning Sun, Aug 3, priced at $308 found 3 days ago

Mon, Aug 18 - Thu, Aug 21

BDL

Bradley Intl.

ORD

O'Hare Intl.

$312 Roundtrip, found 13 hours ago

$312

Roundtrip

found 13 hours ago

Select Spirit Airlines flight, departing Mon, Aug 18 from Bradley Intl. to O'Hare Intl., returning Thu, Aug 21, priced at $312 found 13 hours ago

Mon, Aug 18 - Thu, Aug 21

BDL

Bradley Intl.

ORD

O'Hare Intl.

$318 Roundtrip, found 13 hours ago

$318

Roundtrip

found 13 hours ago

Select Spirit Airlines flight, departing Mon, Aug 18 from Bradley Intl. to O'Hare Intl., returning Thu, Aug 21, priced at $318 found 13 hours ago

Wed, Aug 20 - Thu, Aug 21

BDL

Bradley Intl.

ORD

O'Hare Intl.

$319 Roundtrip, found 13 hours ago

$319

Roundtrip

found 13 hours ago

Select American Airlines flight, departing Wed, Aug 20 from Bradley Intl. to O'Hare Intl., returning Thu, Aug 21, priced at $319 found 13 hours ago

Mon, Aug 18 - Thu, Aug 21

BDL

Bradley Intl.

ORD

O'Hare Intl.

$330 Roundtrip, found 13 hours ago

$330

Roundtrip

found 13 hours ago

Select American Airlines flight, departing Mon, Aug 18 from Bradley Intl. to O'Hare Intl., returning Thu, Aug 21, priced at $330 found 13 hours ago

Thu, Aug 21 - Thu, Aug 21

BDL

Bradley Intl.

MDW

Midway Intl.

$338 Roundtrip, found 13 hours ago

$338

Roundtrip

found 13 hours ago

Select Delta flight, departing Thu, Aug 21 from Bradley Intl. to Midway Intl., returning Thu, Aug 21, priced at $338 found 13 hours ago

Mon, Aug 18 - Thu, Aug 21

BDL

Bradley Intl.

ORD

O'Hare Intl.

$362 Roundtrip, found 13 hours ago

$362

Roundtrip

found 13 hours ago

Select American Airlines flight, departing Mon, Aug 18 from Bradley Intl. to O'Hare Intl., returning Thu, Aug 21, priced at $362 found 13 hours ago

Sun, Aug 17 - Fri, Aug 22

BDL

Bradley Intl.

MDW

Midway Intl.

$366 Roundtrip, found 13 hours ago

$366

Roundtrip

found 13 hours ago

Select Frontier Airlines flight, departing Sun, Aug 17 from Bradley Intl. to Midway Intl., returning Fri, Aug 22, priced at $366 found 13 hours ago