$61 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.

Sun, Oct 19 - Sat, Oct 25
CLE
Hopkins Intl.
MDW
Midway Intl.
$190 Roundtrip, found 3 days ago
$190
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Oct 19 from Hopkins Intl. to Midway Intl., returning Sat, Oct 25, priced at $190 found 3 days ago
Sun, Oct 19 - Sat, Oct 25
CAK
Akron-Canton
ORD
O'Hare Intl.
$322 Roundtrip, found 1 day ago
$322
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Oct 19 from Akron-Canton to O'Hare Intl., returning Sat, Oct 25, priced at $322 found 1 day ago
Sat, Oct 18 - Sun, Oct 19
CLE
Hopkins Intl.
ORD
O'Hare Intl.
$402 Roundtrip, found 4 hours ago
$402
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Oct 18 from Hopkins Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $402 found 4 hours ago

Airfares from $61 One Way, $120 Round Trip from Akron to Chicago

Prices starting at $120 for return flights and $61 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 25 - Thu, Oct 30
CLE
Cleveland
MDW
Chicago
$120 Roundtrip, found 5 days ago
$120
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Oct 25 from Cleveland to Chicago, returning Thu, Oct 30, priced at $120 found 5 days ago
Fri, Nov 7 - Fri, Nov 14
CLE
Cleveland
ORD
Chicago
$163 Roundtrip, found 4 days ago
$163
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Nov 7 from Cleveland to Chicago, returning Fri, Nov 14, priced at $163 found 4 days ago
Tue, Nov 18 - Sat, Nov 29
CAK
Akron
ORD
Chicago
$193 Roundtrip, found 3 days ago
$193
Roundtrip
found 3 days ago
Select United flight, departing Tue, Nov 18 from Akron to Chicago, returning Sat, Nov 29, priced at $193 found 3 days ago
Fri, Nov 14 - Sun, Nov 16
CAK
Akron
RFD
Rockford
$211 Roundtrip, found 3 days ago
$211
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Nov 14 from Akron to Rockford, returning Sun, Nov 16, priced at $211 found 3 days ago
Fri, Feb 13 - Sun, Feb 15
CLE
Cleveland
RFD
Rockford
$226 Roundtrip, found 2 days ago
$226
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Feb 13 from Cleveland to Rockford, returning Sun, Feb 15, priced at $226 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! (2,427 reviews)

Dec 10 - Dec 12

2 night stay

Akron (CAK) to Chicago (ORD)

United • Roundtrip • Coach
Price was $457, price is now $357 per person
$357
per person
found 9 hours ago
One day didn’t receive room service

Reviewed on Sep 2, 2025

Embassy Suites by Hilton Chicago Downtown River North
4.0-star property

Embassy Suites by Hilton Chicago Downtown River North

8.6/10 Excellent! (4,926 reviews)

Dec 10 - Dec 12

2 night stay

Akron (CAK) to Chicago (ORD)

United • Roundtrip • Coach
Price was $436, price is now $378 per person
$378
per person
found 9 hours ago
Awesome breakfast and happy hour

Reviewed on Oct 11, 2025

The Blackstone, Autograph Collection
4.0-star property

The Blackstone, Autograph Collection

9/10 Wonderful! (1,008 reviews)

Dec 10 - Dec 12

2 night stay

Akron (CAK) to Chicago (ORD)

United • Roundtrip • Coach
Price was $468, price is now $429 per person
$429
per person
found 9 hours ago
Elegant, old-fashioned (in a good way) with modern touches. Very quiet, well appointed.

Reviewed on Nov 18, 2023

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Chicago first class flight packages

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

Swissotel - Chicago

9/10 Wonderful! (2,765 reviews)

Dec 10 - Dec 12

2 night stay

Akron (CAK) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $782, price is now $689 per person
$689
per person
found 9 hours ago
All around a great location with incredible views. We stayed in a king suite on the 30th floor with views of both the city and lake thanks to architect that designed the building as a triangle that overlooks the Chicago river.

Reviewed on Sep 3, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,716 reviews)

Dec 10 - Dec 12

2 night stay

Akron (CAK) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $1,167, price is now $948 per person
$948
per person
found 9 hours ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,002 reviews)

Dec 10 - Dec 12

2 night stay

Akron (CAK) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $1,115, price is now $946 per person
$946
per person
found 9 hours ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.

Reviewed on Sep 13, 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.

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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.