$91 Cheap flight deals from Modesto (SMF) to Chicago (CHI)

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This Weekend's Flight Deals from Modesto 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, Mar 7 - Tue, Mar 10
SMF
Sacramento Intl.
ORD
O'Hare Intl.
$365 Roundtrip, found 4 days ago
$365
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Sat, Mar 7 from Sacramento Intl. to O'Hare Intl., returning Tue, Mar 10, priced at $365 found 4 days ago
Fri, Mar 6 - Tue, Mar 17
SMF
Sacramento Intl.
MDW
Midway Intl.
$369 Roundtrip, found 22 hours ago
$369
Roundtrip
found 22 hours ago
Select Delta flight, departing Fri, Mar 6 from Sacramento Intl. to Midway Intl., returning Tue, Mar 17, priced at $369 found 22 hours ago
Sun, Mar 8 - Tue, Mar 31
OAK
Oakland Intl.
ORD
O'Hare Intl.
$523 Roundtrip, found 5 days ago
$523
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Sun, Mar 8 from Oakland Intl. to O'Hare Intl., returning Tue, Mar 31, priced at $523 found 5 days ago
Sat, Mar 7 - Mon, Mar 9
OAK
Oakland Intl.
MDW
Midway Intl.
$706 Roundtrip, found 5 days ago
$706
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Mar 7 from Oakland Intl. to Midway Intl., returning Mon, Mar 9, priced at $706 found 5 days ago

Airfares from $91 One Way, $181 Round Trip from Modesto to Chicago

Prices starting at $181 for return flights and $91 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, Apr 22 - Mon, Apr 27
OAK
Oakland
MDW
Chicago
$181 Roundtrip, found 6 days ago
$181
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Apr 22 from Oakland to Chicago, returning Mon, Apr 27, priced at $181 found 6 days ago
Wed, Apr 15 - Sat, Apr 18
SMF
Sacramento
ORD
Chicago
$191 Roundtrip, found 4 days ago
$191
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Wed, Apr 15 from Sacramento to Chicago, returning Sat, Apr 18, priced at $191 found 4 days ago
Wed, Apr 22 - Mon, Apr 27
OAK
Oakland
MDW
Chicago
$191 Roundtrip, found 6 days ago
$191
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Apr 22 from Oakland to Chicago, returning Mon, Apr 27, priced at $191 found 6 days ago
Mon, May 4 - Wed, May 13
SMF
Sacramento
ORD
Chicago
$200 Roundtrip, found 2 days ago
$200
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, May 4 from Sacramento to Chicago, returning Wed, May 13, priced at $200 found 2 days ago
Tue, May 12 - Tue, May 19
OAK
Oakland
ORD
Chicago
$234 Roundtrip, found 4 days ago
$234
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Tue, May 12 from Oakland to Chicago, returning Tue, May 19, priced at $234 found 4 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
4.0-star property

Eurostars Magnificent Mile

9/10 Wonderful! (3,271 reviews)

Apr 24 - Apr 27

3 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Price was $757, price is now $562 per person
$562
per person
found 1 day ago
In convenient area either by walking or uber

Reviewed on Oct 18, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Apr 24 - Apr 27

3 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Price was $855, price is now $594 per person
$594
per person
found 1 day ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

9.2/10 Wonderful! (413 reviews)

Apr 7 - Apr 11

4 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Price was $858, price is now $661 per person
$661
per person
found 1 day ago
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More About Flying To Chicago from Modesto

Route Information for Flights from Modesto to Chicago

Origin Airport IATA Code
SMF
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Modesto to Chicago

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You can always find affordable flights from Modesto to Chicago on Orbitz. Use different airlines to book arrival and departure flights, take advantage of vacation package deals, and secure exclusive rewards.

Frequently asked questions

Are there non-stop flights from Modesto to Chicago?
United Airlines and American Airlines offer direct flights from Sacramento, CA (SMF-Sacramento Intl.) to O'Hare Airport, which means you won't need to stress about changing planes or being hopelessly bored during a stopover.
What is the shortest flight from Modesto to Chicago?
With the journey from Oakland, CA (OAK-Oakland Intl.) to Chicago, IL (MDW-Midway Intl.) taking a minimum of 4 hours and 35 minutes, you'll have plenty of time to enjoy the flying experience. Grab a glass of wine and get cozy in your seat with a fascinating movie or novel.
What airlines fly from Modesto to Chicago most frequently?
United Airlines (UA) is one of the carriers with the most flights from SMF to O'Hare Airport. It offers 112 flights each month on this route. Taking a vacation is one of life's greatest pleasures, and this carrier will get you where you need to go. American Airlines (AA) also flies from Modesto to Chicago. It's another reliable choice and offers 34 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.