Flights from Chicago to Gateway

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, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$318 Roundtrip, found 19 hours ago

$318

Roundtrip

found 19 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $318 found 19 hours ago

Thu, Aug 21 - Sun, Aug 24

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$318 Roundtrip, found 3 hours ago

$318

Roundtrip

found 3 hours ago

Select Hawaiian Airlines flight, departing Thu, Aug 21 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Sun, Aug 24, priced at $318 found 3 hours ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$318 Roundtrip, found 19 hours ago

$318

Roundtrip

found 19 hours ago

Select Alaska Airlines flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $318 found 19 hours ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$328 Roundtrip, found 19 hours ago

$328

Roundtrip

found 19 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $328 found 19 hours ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$338 Roundtrip, found 19 hours ago

$338

Roundtrip

found 19 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $338 found 19 hours ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$338 Roundtrip, found 19 hours ago

$338

Roundtrip

found 19 hours ago

Select Delta flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $338 found 19 hours ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$356 Roundtrip, found 19 hours ago

$356

Roundtrip

found 19 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $356 found 19 hours ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$358 Roundtrip, found 19 hours ago

$358

Roundtrip

found 19 hours ago

Select Delta flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $358 found 19 hours ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$365 Roundtrip, found 19 hours ago

$365

Roundtrip

found 19 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $365 found 19 hours ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$368 Roundtrip, found 19 hours ago

$368

Roundtrip

found 19 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $368 found 19 hours ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$373 Roundtrip, found 19 hours ago

$373

Roundtrip

found 19 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $373 found 19 hours ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$379 Roundtrip, found 19 hours ago

$379

Roundtrip

found 19 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $379 found 19 hours ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$380 Roundtrip, found 19 hours ago

$380

Roundtrip

found 19 hours ago

Select Delta flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $380 found 19 hours ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$381 Roundtrip, found 19 hours ago

$381

Roundtrip

found 19 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $381 found 19 hours ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$383 Roundtrip, found 19 hours ago

$383

Roundtrip

found 19 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $383 found 19 hours ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$388 Roundtrip, found 19 hours ago

$388

Roundtrip

found 19 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $388 found 19 hours ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$389 Roundtrip, found 19 hours ago

$389

Roundtrip

found 19 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $389 found 19 hours ago

Tue, Dec 16 - Wed, Dec 24

MDW

Midway Intl.

ANC

Ted Stevens Anchorage Intl.

$390 Roundtrip, found 6 days ago

$390

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Dec 16 from Midway Intl. to Ted Stevens Anchorage Intl., returning Wed, Dec 24, priced at $390 found 6 days ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$391 Roundtrip, found 19 hours ago

$391

Roundtrip

found 19 hours ago

Select United flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $391 found 19 hours ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$516 Roundtrip, found 19 hours ago

$516

Roundtrip

found 19 hours ago

Select American Airlines flight, departing Wed, Aug 20 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Wed, Aug 27, priced at $516 found 19 hours ago