Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

Cheap flights from Anchorage (ANC) to Chicago (CHI)

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Lowest round trip fares by airline from Anchorage and Chicago

Cheapest prices ($159 One Way, $303 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Jul 16
ANC
Anchorage
ORD
Chicago
$159
Alaska Airlines
Tue, Aug 31
ANC
Anchorage
ORD
Chicago
$160
Bargain Flight
Thu, Sep 16
ANC
Anchorage
ORD
Chicago
$163
American Airlines
Sun, Aug 22
ANC
Anchorage
ORD
Chicago
$163
United
Sun, Apr 17
ANC
Anchorage
MDW
Chicago
$168
Delta
Wed, Nov 3 - Sat, Nov 6
ANC
Anchorage
ORD
Chicago
$303
Alaska Airlines
Tue, Aug 31 - Tue, Sep 14
ANC
Anchorage
ORD
Chicago
$310
Bargain Flight
Wed, Nov 3 - Sat, Nov 6
ANC
Anchorage
ORD
Chicago
$312
Alaska Airlines
Wed, Sep 29 - Sun, Oct 3
ANC
Anchorage
ORD
Chicago
$319
Alaska Airlines
Tue, Aug 31 - Tue, Sep 14
ANC
Anchorage
ORD
Chicago
$323
United

Great Deals On Cheap Hotels in Chicago

Freehand Chicago

Freehand Chicago

3.5 out of 5
19 East Ohio Street, Chicago, IL
The price is $85 per night from Jun 29 to Jun 29
Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary ...
4.3/5Excellent! (15 reviews)
"I like the bunk beds- so interesting. I love the location. It is close to everything. You are in the heart of the city with lots of activities to do! The staff from day one have been so rude, so cold in attitude just unpleasant but I have tried to beasrespectful and polite as I can possibly be - ..."

Reviewed on Sep 21, 2020

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
The price is $123 per night from Jun 24 to Jun 24
Located in The Loop, this hotel is steps from Columbia College Chicago, Grant Park, and State Street. Art Institute of Chicago and Buckingham Fountain are also ...
3/5 (10 reviews)
"I liked the close proximity to downtown, Chicago. The two restaurants on the property as well as close parking in which you would need to pay."

Reviewed on Sep 25, 2020

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
The price is $45 per night from Jun 28 to Jun 28
Situated in Elk Grove Village, this motel is 2.1 mi (3.3 km) from Lake Park and 2.8 mi (4.6 km) from Allstate Arena. Apache Park is 2.9 mi (4.7 km) away.
3.8/5Good! (13 reviews)
"Really nice and clean place. The parking lot was clear."

Reviewed on Feb 23, 2021

Motel 6 Elk Grove Village, IL - O'Hare
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Flights Review

Sep 27, 2018

The flight was hot. Normally I ride using the blanket and a jacket.

A verified traveler
Anchorage to Chicago · United

Fly From Anchorage to Chicago

Origin Anchorage
Destination Chicago
Number of Daily Flights 6
Earliest Flight Departure Date Jul 1
Latest Flight Departure Date Jul 1
Popular Airlines Alaska Airlines

Cheap flights from Anchorage to Chicago

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Relax in Chicago With Confidence and Convenience

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.