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

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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 5 - Wed, Jul 9
CLE
Hopkins Intl.
MDW
Midway Intl.
$275 Roundtrip, found 2 days ago
$275
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Jul 5 from Hopkins Intl. to Midway Intl., returning Wed, Jul 9, priced at $275 found 2 days ago
Sat, Jul 5 - Wed, Jul 23
CAK
Akron-Canton
ORD
O'Hare Intl.
$298 Roundtrip, found 3 days ago
$298
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jul 5 from Akron-Canton to O'Hare Intl., returning Wed, Jul 23, priced at $298 found 3 days ago
Sun, Jul 6 - Tue, Jul 8
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$361 Roundtrip, found 5 hours ago
$361
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sun, Jul 6 from Hopkins Intl. to O'Hare Intl., returning Tue, Jul 8, priced at $361 found 5 hours ago

Airfares from $58 One Way, $127 Round Trip from Akron to Chicago

Prices starting at $127 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.

Sat, Oct 11 - Sat, Oct 18
CLE
Cleveland
ORD
Chicago
$127 Roundtrip, found 8 hours ago
$127
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Sat, Oct 11 from Cleveland to Chicago, returning Sat, Oct 18, priced at $127 found 8 hours ago
Sat, Oct 11 - Sat, Oct 18
CLE
Cleveland
ORD
Chicago
$127 Roundtrip, found 8 hours ago
$127
Roundtrip
found 8 hours ago
Select United flight, departing Sat, Oct 11 from Cleveland to Chicago, returning Sat, Oct 18, priced at $127 found 8 hours ago
Sat, Oct 11 - Sat, Oct 18
CLE
Cleveland
ORD
Chicago
$129 Roundtrip, found 8 hours ago
$129
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Sat, Oct 11 from Cleveland to Chicago, returning Sat, Oct 18, priced at $129 found 8 hours ago
Thu, Aug 28 - Sat, Aug 30
CLE
Cleveland
MDW
Chicago
$132 Roundtrip, found 6 days ago
$132
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Aug 28 from Cleveland to Chicago, returning Sat, Aug 30, priced at $132 found 6 days ago
Thu, Oct 2 - Mon, Oct 6
CLE
Cleveland
ORD
Chicago
$134 Roundtrip, found 3 days ago
$134
Roundtrip
found 3 days ago
Select United flight, departing Thu, Oct 2 from Cleveland to Chicago, returning Mon, Oct 6, priced at $134 found 3 days ago

Chicago economy flight packages

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

Arlo Chicago

9.2/10 Wonderful! (1,769 reviews)

Aug 6 - Aug 9

3 night stay

Akron (CAK) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
per person
found 22 hours ago
Fantastic stay, amazing location.

Reviewed on Jun 25, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,623 reviews)

Aug 6 - Aug 9

3 night stay

Akron (CAK) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
per person
found 22 hours ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!

Reviewed on Jun 16, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,065 reviews)

Aug 6 - Aug 9

3 night stay

Akron (CAK) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
per person
found 22 hours ago
Our second time. Here, highly recommended

Reviewed on Mar 3, 2025

Don't see what you're looking for?
See all available trips from Akron to Chicago
View all trips

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, Aer Lingus, Emirates, Copa Airlines, Swiss, Air New Zealand, United Airlines, Alaska Airlines, Cathay Pacific, Avianca, Turkish Airlines, Royal Jordanian, Finnair, Iberia, ANA, Lufthansa, Gulf Air, British Airways
Earliest Flight Arrival
10:05AM UTC
Latest Flight Arrival
1:30AM UTC

Akron to Chicago

The perfect trip begins with Orbitz. From booking your flights from Akron to Chicago to finding the best hotels, Orbitz has got it covered.

Stress-free Searching

With an easy to use system, Orbitz takes the stress and expense out of travel. Not only does Orbitz match your Akron to Chicago flights to your ideal hotel, the Display Matrix shows your deals and discounts, including free nights and other savings.

Be One Step Ahead

Need to know what is going on at the airport before you get there? With Orbitz’s free alerts service, you can quickly find out about any booking changes, or flight from Akron to Chicago disruptions, saving you hours of wasted time. And if you are being picked up at the airport after your Akron to Chicago flights, have alerts sent straight to your contact’s mobile phone or email.

Cutting-Edge Mobile Tools

Find the best price on flights from Akron to Chicago with Orbitz’s mobile apps for iPhone and Android. Use m.orbitz.com on your mobile browser to check your gate, baggage allowance and delays, or find exclusive deals on hotels only available to mobile users.

We Work, you Rest and Play

Not only does booking with us ensure guaranteed low prices, but Orbitz does the hard work, leaving you to relax. Just tell us what you want, from Akron to Chicago flights, to great deals on hotels and car rental, and activities and tours, and we will do all the rest.

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.