$49 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.

Sat, Jul 25 - Wed, Jul 29
CAK
Akron-Canton
ORD
O'Hare Intl.
$334 Roundtrip, found 4 days ago
$334
Roundtrip
found 4 days ago
Select United flight, departing Sat, Jul 25 from Akron-Canton to O'Hare Intl., returning Wed, Jul 29, priced at $334 found 4 days ago
Sun, Jul 26 - Fri, Jul 31
CLE
Hopkins Intl.
MDW
Midway Intl.
$351 Roundtrip, found 18 hours ago
$351
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Sun, Jul 26 from Hopkins Intl. to Midway Intl., returning Fri, Jul 31, priced at $351 found 18 hours ago
Sun, Jul 26 - Mon, Jul 27
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$427 Roundtrip, found 10 hours ago
$427
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sun, Jul 26 from Hopkins Intl. to O'Hare Intl., returning Mon, Jul 27, priced at $427 found 10 hours ago

Airfares from $49 One Way, $97 Round Trip from Akron to Chicago

Prices starting at $97 for return flights and $49 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.

Mon, Aug 17 - Tue, Aug 18
CLE
Cleveland
MDW
Chicago
$97 Roundtrip, found 19 hours ago
$97
Roundtrip
found 19 hours ago
Select Southwest Airlines flight, departing Mon, Aug 17 from Cleveland to Chicago, returning Tue, Aug 18, priced at $97 found 19 hours ago
Tue, Oct 6 - Thu, Oct 8
CLE
Cleveland
ORD
Chicago
$97 Roundtrip, found 7 hours ago
$97
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Tue, Oct 6 from Cleveland to Chicago, returning Thu, Oct 8, priced at $97 found 7 hours ago
Tue, Aug 18 - Sat, Aug 22
CLE
Cleveland
ORD
Chicago
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select United flight, departing Tue, Aug 18 from Cleveland to Chicago, returning Sat, Aug 22, priced at $97 found 1 day ago
Tue, Oct 6 - Thu, Oct 8
CLE
Cleveland
ORD
Chicago
$157 Roundtrip, found 7 hours ago
$157
Roundtrip
found 7 hours ago
Select Delta flight, departing Tue, Oct 6 from Cleveland to Chicago, returning Thu, Oct 8, priced at $157 found 7 hours ago
Wed, Aug 19 - Sat, Aug 22
CLE
Cleveland
RFD
Rockford
$198 Roundtrip, found 2 days ago
$198
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Aug 19 from Cleveland to Rockford, returning Sat, Aug 22, priced at $198 found 2 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (4,714 reviews)

Aug 28 - Aug 31

3 night stay

Akron (CAK) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,147, price is now $741 per person
$741
per person
found 1 day ago
Very clean, high end hotel.

Reviewed on Jul 23, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,603 reviews)

Aug 28 - Aug 31

3 night stay

Akron (CAK) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,224, price is now $880 per person
$880
per person
found 1 day ago
Hotel was nice and close to the amenities of the pier. Only downside was most attractions are in the city which makes this location not as ideal.

Reviewed on Jul 22, 2026

Thompson Chicago, by Hyatt
4.5-star property

Thompson Chicago, by Hyatt

9.2/10 Wonderful! (1,392 reviews)

Aug 28 - Aug 31

3 night stay

Akron (CAK) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,367, price is now $1,031 per person
$1,031
per person
found 1 day ago
Great staff and nice room

Reviewed on Jul 22, 2026

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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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Akron to Chicago

If you are looking to get guaranteed low prices for Akron to Chicago flights then Orbitz is the place to go. We use cutting edge mobile tools to find the best deals on air tickets and to keep you updated on delays and changes.

Get Package Savings by Booking Flights and Hotels at the Same Time

Using the Orbitz Matrix display, you can see how much you will save on flights from Akron to Chicago if the discount fare is combined with a hotel. You can also look at hotel reviews, photos and maps of the area, so it will be convenient to make your budget travel plans.

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Orbitz can assist all businesses from the small to major corporations with discounts on flights from Akron to Chicago. We fine- tune your needs for Akron to Chicago flights and optimize your plans by assessing your business and coming up with ways for you to save on air tickets.

Using Online Check-In Makes Flying Simple

You can use the Orbitz website to check-in for your flights from Akron to Chicago. You can also make changes to your schedule or even cancel a flight.

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.

More Destinations

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.