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, just found

$318

Roundtrip

just found

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

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$318 Roundtrip, just found

$318

Roundtrip

just found

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

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$328 Roundtrip, just found

$328

Roundtrip

just found

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

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$338 Roundtrip, just found

$338

Roundtrip

just found

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

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$338 Roundtrip, just found

$338

Roundtrip

just found

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

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$356 Roundtrip, just found

$356

Roundtrip

just found

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

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$358 Roundtrip, just found

$358

Roundtrip

just found

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

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$365 Roundtrip, just found

$365

Roundtrip

just found

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

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$368 Roundtrip, just found

$368

Roundtrip

just found

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

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$373 Roundtrip, just found

$373

Roundtrip

just found

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

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$379 Roundtrip, just found

$379

Roundtrip

just found

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

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$380 Roundtrip, just found

$380

Roundtrip

just found

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

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$381 Roundtrip, just found

$381

Roundtrip

just found

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

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$383 Roundtrip, just found

$383

Roundtrip

just found

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

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$388 Roundtrip, just found

$388

Roundtrip

just found

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

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$389 Roundtrip, just found

$389

Roundtrip

just found

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

Tue, Dec 16 - Wed, Dec 24

MDW

Midway Intl.

ANC

Ted Stevens Anchorage Intl.

$390 Roundtrip, found 5 days ago

$390

Roundtrip

found 5 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 5 days ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$391 Roundtrip, just found

$391

Roundtrip

just found

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

Sat, Aug 23 - Sun, Aug 24

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$395 Roundtrip, found 4 days ago

$395

Roundtrip

found 4 days ago

Select Hawaiian Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Ted Stevens Anchorage Intl., returning Sun, Aug 24, priced at $395 found 4 days ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

ANC

Ted Stevens Anchorage Intl.

$516 Roundtrip, just found

$516

Roundtrip

just found

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