$89 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, Feb 28 - Tue, Mar 10
SMF
Sacramento Intl.
MDW
Midway Intl.
$325 Roundtrip, found 2 days ago
$325
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Feb 28 from Sacramento Intl. to Midway Intl., returning Tue, Mar 10, priced at $325 found 2 days ago
Fri, Feb 27 - Mon, Mar 9
SMF
Sacramento Intl.
ORD
O'Hare Intl.
$345 Roundtrip, found 12 hours ago
$345
Roundtrip
found 12 hours ago
Select Alaska Airlines flight, departing Fri, Feb 27 from Sacramento Intl. to O'Hare Intl., returning Mon, Mar 9, priced at $345 found 12 hours ago
Fri, Feb 27 - Mon, Mar 2
OAK
Oakland Intl.
ORD
O'Hare Intl.
$495 Roundtrip, found 3 days ago
$495
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Fri, Feb 27 from Oakland Intl. to O'Hare Intl., returning Mon, Mar 2, priced at $495 found 3 days ago

Airfares from $89 One Way, $195 Round Trip from Modesto to Chicago

Prices starting at $195 for return flights and $89 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 29 - Tue, May 5
SMF
Sacramento
ORD
Chicago
$195 Roundtrip, found 22 hours ago
$195
Roundtrip
found 22 hours ago
Select Alaska Airlines flight, departing Wed, Apr 29 from Sacramento to Chicago, returning Tue, May 5, priced at $195 found 22 hours ago
Mon, Apr 27 - Thu, May 7
SMF
Sacramento
ORD
Chicago
$200 Roundtrip, found 6 hours ago
$200
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Mon, Apr 27 from Sacramento to Chicago, returning Thu, May 7, priced at $200 found 6 hours ago
Tue, May 12 - Mon, May 18
OAK
Oakland
ORD
Chicago
$214 Roundtrip, found 9 hours ago
$214
Roundtrip
found 9 hours ago
Select Alaska Airlines flight, departing Tue, May 12 from Oakland to Chicago, returning Mon, May 18, priced at $214 found 9 hours ago
Mon, Apr 27 - Thu, Apr 30
OAK
Oakland
MDW
Chicago
$217 Roundtrip, found 5 days ago
$217
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Apr 27 from Oakland to Chicago, returning Thu, Apr 30, priced at $217 found 5 days ago
Tue, Apr 28 - Sat, May 2
SMF
Sacramento
MDW
Chicago
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Apr 28 from Sacramento to Chicago, returning Sat, May 2, priced at $237 found 1 day 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! (2,790 reviews)

Apr 10 - Apr 14

4 night stay

Oakland (OAK) to Chicago (ORD)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $965, price is now $610 per person
$610
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! (347 reviews)

Apr 10 - Apr 14

4 night stay

Oakland (OAK) to Chicago (ORD)

Delta • Non-stop roundtrip • Coach
Price was $898, price is now $656 per person
$656
per person
found 1 day ago
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (380 reviews)

Apr 10 - Apr 14

4 night stay

Oakland (OAK) to Chicago (ORD)

Delta • Non-stop roundtrip • Coach
Price was $1,048, price is now $805 per person
$805
per person
found 1 day ago
We always love staying here. Such great service and nice accommodations.

Reviewed on Nov 20, 2025

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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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Our iPhone and Android mobile apps can be used to compare and book flights from Modesto to Chicago. These apps are perfect for checking the status of flights, gate and baggage claims details, car rental rates, and for receiving alerts on special savings that are exclusive to mobile users. Mobile app users can even score great rates when booking hotel rooms. You can compare hotels, virtually view photo galleries, and check out user reviews using the app, as well as find out which ones are closest to you.

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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.