$59 Cheap flight deals from Chicago (CHI) to Westlake (CLE)

This Weekend's Flight Deals from Chicago to Westlake

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Oct 4 - Sun, Oct 11
ORD
O'Hare Intl.
CLE
Hopkins Intl.
$343 Roundtrip, found 5 days ago
$343
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Oct 4 from O'Hare Intl. to Hopkins Intl., returning Sun, Oct 11, priced at $343 found 5 days ago
Fri, Oct 2 - Mon, Oct 5
MDW
Midway Intl.
CLE
Hopkins Intl.
$531 Roundtrip, found 6 days ago
$531
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Oct 2 from Midway Intl. to Hopkins Intl., returning Mon, Oct 5, priced at $531 found 6 days ago

Airfares from $59 One Way, $117 Round Trip from Chicago to Westlake

Prices starting at $117 for return flights and $59 for one-way flights to Westlake were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Nov 21 - Mon, Nov 23
ORD
Chicago
CLE
Cleveland
$117 Roundtrip, found 13 hours ago
$117
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sat, Nov 21 from Chicago to Cleveland, returning Mon, Nov 23, priced at $117 found 13 hours ago
Thu, Jan 21 - Sat, Jan 23
MDW
Chicago
CLE
Cleveland
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Jan 21 from Chicago to Cleveland, returning Sat, Jan 23, priced at $117 found 1 day ago
Sat, Nov 7 - Mon, Nov 9
ORD
Chicago
CLE
Cleveland
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select United flight, departing Sat, Nov 7 from Chicago to Cleveland, returning Mon, Nov 9, priced at $117 found 1 day ago
Sat, Nov 21 - Mon, Nov 23
ORD
Chicago
CLE
Cleveland
$119 Roundtrip, found 13 hours ago
$119
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sat, Nov 21 from Chicago to Cleveland, returning Mon, Nov 23, priced at $119 found 13 hours ago
Sat, Nov 21 - Mon, Nov 23
ORD
Chicago
CLE
Cleveland
$120 Roundtrip, found 13 hours ago
$120
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sat, Nov 21 from Chicago to Cleveland, returning Mon, Nov 23, priced at $120 found 13 hours ago

Westlake economy flight packages

Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott Cleveland Beachwood
3.0-star property

Residence Inn by Marriott Cleveland Beachwood

8.4/10 Very Good! (1,003 reviews)

Oct 30 - Nov 1

2 night stay

Chicago (CHI) to Cleveland (CLE)

Southwest Airlines • Coach

Cleveland (CLE) to Chicago (CHI)

Frontier Airlines • Coach
Price was $391, price is now $350 per person
$350
per person
found 1 day ago
The hotel is in a good location, staff is very friendly. Rooms can use an update

Reviewed on Sep 22, 2026

Holiday Inn Cleveland Clinic by IHG
3.0-star property

Holiday Inn Cleveland Clinic by IHG

8.8/10 Excellent! (1,498 reviews)

Oct 30 - Nov 1

2 night stay

Chicago (CHI) to Cleveland (CLE)

Southwest Airlines • Coach

Cleveland (CLE) to Chicago (CHI)

Frontier Airlines • Coach
Price was $458, price is now $392 per person
$392
per person
found 1 day ago
Great

Reviewed on Sep 25, 2026

Kimpton Schofield Hotel by IHG
4.5-star property

Kimpton Schofield Hotel by IHG

9/10 Wonderful! (1,041 reviews)

Oct 30 - Nov 1

2 night stay

Chicago (CHI) to Cleveland (CLE)

Southwest Airlines • Coach

Cleveland (CLE) to Chicago (CHI)

Frontier Airlines • Coach
Price was $553, price is now $480 per person
$480
per person
found 1 day ago

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