$55 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, Jun 21 - Sat, Jun 28
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 17 hours ago
$172
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sat, Jun 21 from Hopkins Intl. to O'Hare Intl., returning Sat, Jun 28, priced at $172 found 17 hours ago
Sun, Jun 22 - Sun, Jun 29
CAK
Akron-Canton
ORD
O'Hare Intl.
$197 Roundtrip, found 6 days ago
$197
Roundtrip
found 6 days ago
Select United flight, departing Sun, Jun 22 from Akron-Canton to O'Hare Intl., returning Sun, Jun 29, priced at $197 found 6 days ago
Sun, Jun 22 - Wed, Jun 25
CLE
Hopkins Intl.
MDW
Midway Intl.
$405 Roundtrip, found 2 days ago
$405
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sun, Jun 22 from Hopkins Intl. to Midway Intl., returning Wed, Jun 25, priced at $405 found 2 days ago

Airfares from $55 One Way, $111 Round Trip from Akron to Chicago

Prices starting at $111 for return flights and $55 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.

Tue, Aug 5 - Thu, Aug 7
CLE
Cleveland
ORD
Chicago
$111 Roundtrip, found 2 days ago
$111
Roundtrip
found 2 days ago
Select United flight, departing Tue, Aug 5 from Cleveland to Chicago, returning Thu, Aug 7, priced at $111 found 2 days ago
Tue, Aug 5 - Thu, Aug 7
CLE
Cleveland
ORD
Chicago
$111 Roundtrip, found 2 days ago
$111
Roundtrip
found 2 days ago
Select United flight, departing Tue, Aug 5 from Cleveland to Chicago, returning Thu, Aug 7, priced at $111 found 2 days ago
Thu, Dec 4 - Sat, Dec 6
CLE
Cleveland
MDW
Chicago
$130 Roundtrip, found 3 days ago
$130
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Dec 4 from Cleveland to Chicago, returning Sat, Dec 6, priced at $130 found 3 days ago
Wed, Aug 13 - Sat, Aug 16
CLE
Cleveland
ORD
Chicago
$130 Roundtrip, found 3 days ago
$130
Roundtrip
found 3 days ago
Select United flight, departing Wed, Aug 13 from Cleveland to Chicago, returning Sat, Aug 16, priced at $130 found 3 days ago
Thu, Sep 18 - Sat, Sep 20
CLE
Cleveland
ORD
Chicago
$144 Roundtrip, found 1 day ago
$144
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Sep 18 from Cleveland to Chicago, returning Sat, Sep 20, priced at $144 found 1 day ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North
4.0-star property

Embassy Suites by Hilton Chicago Downtown River North

8.4/10 Very Good! (4,155 reviews)

Jul 26 - Jul 30

4 night stay

Akron (CAK) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Excellent stay. Room was clean and well-designed for our family. Fantastic complimentary breakfast every morning.

Reviewed on Jun 13, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,602 reviews)

Jul 26 - Jul 30

4 night stay

Akron (CAK) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Perfect stay. Great hotel. Only complaint is the death spot in the bedroom. Gross looking stain on the floor: other than that- perfect.

Reviewed on Jun 1, 2025

Nobu Hotel Chicago
5.0-star property

Nobu Hotel Chicago

9.4/10 Exceptional! (677 reviews)

Jul 26 - Jul 30

4 night stay

Akron (CAK) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Best hotel I ever been in

Reviewed on Jul 16, 2024

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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

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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.