$58 Cheap flight deals from Akron (CLE) to Chicago (CHI)

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This Weekend's Flight Deals from Akron to Chicago

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.

Fri, Jul 4 - Sat, Jul 5
CLE
Hopkins Intl.
MDW
Midway Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 4 from Hopkins Intl. to Midway Intl., returning Sat, Jul 5, priced at $217 found 1 day ago
Sat, Jul 5 - Wed, Jul 9
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$281 Roundtrip, just found
$281
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jul 5 from Hopkins Intl. to O'Hare Intl., returning Wed, Jul 9, priced at $281 just found
Fri, Jul 4 - Sat, Jul 5
CAK
Akron-Canton
ORD
O'Hare Intl.
$323 Roundtrip, found 2 hours ago
$323
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Fri, Jul 4 from Akron-Canton to O'Hare Intl., returning Sat, Jul 5, priced at $323 found 2 hours ago

Airfares from $58 One Way, $129 Round Trip from Akron to Chicago

Prices starting at $129 for return flights and $58 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Sep 10 - Wed, Sep 17
CLE
Cleveland
ORD
Chicago
$129 Roundtrip, found 3 days ago
$129
Roundtrip
found 3 days ago
Select United flight, departing Wed, Sep 10 from Cleveland to Chicago, returning Wed, Sep 17, priced at $129 found 3 days ago
Tue, Sep 2 - Wed, Sep 3
CLE
Cleveland
ORD
Chicago
$131 Roundtrip, found 3 days ago
$131
Roundtrip
found 3 days ago
Select United flight, departing Tue, Sep 2 from Cleveland to Chicago, returning Wed, Sep 3, priced at $131 found 3 days ago
Sat, Jul 19 - Wed, Jul 23
CLE
Cleveland
ORD
Chicago
$149 Roundtrip, found 6 hours ago
$149
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sat, Jul 19 from Cleveland to Chicago, returning Wed, Jul 23, priced at $149 found 6 hours ago
Thu, Aug 28 - Sat, Aug 30
CLE
Cleveland
ORD
Chicago
$177 Roundtrip, found 9 hours ago
$177
Roundtrip
found 9 hours ago
Select Delta flight, departing Thu, Aug 28 from Cleveland to Chicago, returning Sat, Aug 30, priced at $177 found 9 hours ago
Fri, Nov 7 - Mon, Nov 10
CAK
Akron
ORD
Chicago
$189 Roundtrip, found 6 days ago
$189
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Nov 7 from Akron to Chicago, returning Mon, Nov 10, priced at $189 found 6 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

8.6/10 Excellent! (1,781 reviews)

Aug 21 - Aug 23

2 night stay

Akron (CAK) to Chicago (ORD)

American Airlines • Non-stop roundtrip • Coach
per person
found 3 hours ago
came in for the weekend. great location. room was perfect. staff super friendly. will stay again!

Reviewed on Apr 28, 2025

Art Villa
5.0-star property

Art Villa

No reviews

Aug 21 - Aug 23

2 night stay

Akron (CAK) to Chicago (ORD)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 3 hours ago
Swissotel - Chicago
4.5-star property

Swissotel - Chicago

8.8/10 Excellent! (2,274 reviews)

Aug 21 - Aug 23

2 night stay

Akron (CAK) to Chicago (ORD)

American Airlines • Non-stop roundtrip • Coach
per person
found 3 hours ago
Clean and attentive staff

Reviewed on Jun 21, 2025

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More About Flying To Chicago from Akron

Route Information for Flights from Akron to Chicago

Origin Airport IATA Code
CLE
Destination Airport IATA Code
CHI
Distance
315 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Austrian, Aer Lingus, Emirates, Copa Airlines, Air New Zealand, Swiss, United Airlines, Alaska Airlines, Avianca, Turkish Airlines, Royal Jordanian, Iberia, ANA, Lufthansa, Gulf Air, British Airways
Earliest Flight Arrival
7:47AM UTC
Latest Flight Arrival
9:05PM UTC

Akron to Chicago

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Frequently asked questions

Are there non-stop flights from Akron to Chicago?
There are two airlines that offer nonstop flights from Cleveland Hopkins Intl. Airport to O'Hare Intl. Airport (ORD). Lock in your seat now with United Airlines or American Airlines.
What is the shortest flight from Akron to Chicago?
The trip from Akron to Chicago can be as fast as 1 hour and 24 minutes. With a short and sweet flight time like this, why not round up some friends and take off on a spur-of-the-moment getaway?
What airlines fly from Akron to Chicago most frequently?
There are a couple of airlines offering the most frequent flights from CLE to Chicago, IL (ORD-O'Hare Intl.), including United Airlines (UA). A top pick for many travelers, it operates 221 flights on this route each month. American Airlines (AA) also operates services from Akron to Chicago. It's another excellent choice and has 160 flights every month.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.