$117 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, Sep 12 - Wed, Sep 16
SMF
Sacramento Intl.
ORD
O'Hare Intl.
$334 Roundtrip, just found
$334
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Sep 12 from Sacramento Intl. to O'Hare Intl., returning Wed, Sep 16, priced at $334 just found
Fri, Sep 11 - Mon, Sep 14
OAK
Oakland Intl.
ORD
O'Hare Intl.
$386 Roundtrip, found 1 hour ago
$386
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Sep 11 from Oakland Intl. to O'Hare Intl., returning Mon, Sep 14, priced at $386 found 1 hour ago
Fri, Sep 11 - Mon, Sep 14
SMF
Sacramento Intl.
MDW
Midway Intl.
$476 Roundtrip, found 3 days ago
$476
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Sep 11 from Sacramento Intl. to Midway Intl., returning Mon, Sep 14, priced at $476 found 3 days ago
Fri, Sep 11 - Sun, Sep 13
OAK
Oakland Intl.
MDW
Midway Intl.
$498 Roundtrip, found 2 days ago
$498
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Sep 11 from Oakland Intl. to Midway Intl., returning Sun, Sep 13, priced at $498 found 2 days ago

Airfares from $117 One Way, $218 Round Trip from Modesto to Chicago

Prices starting at $218 for return flights and $117 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.

Mon, Oct 12 - Fri, Oct 16
SMF
Sacramento
ORD
Chicago
$218 Roundtrip, found 13 hours ago
$218
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Mon, Oct 12 from Sacramento to Chicago, returning Fri, Oct 16, priced at $218 found 13 hours ago
Mon, Oct 19 - Mon, Oct 26
SMF
Sacramento
ORD
Chicago
$234 Roundtrip, found 1 day ago
$234
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Oct 19 from Sacramento to Chicago, returning Mon, Oct 26, priced at $234 found 1 day ago
Tue, Nov 10 - Thu, Nov 12
OAK
Oakland
ORD
Chicago
$253 Roundtrip, found 3 days ago
$253
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Tue, Nov 10 from Oakland to Chicago, returning Thu, Nov 12, priced at $253 found 3 days ago
Mon, Oct 5 - Fri, Oct 9
OAK
Oakland
MDW
Chicago
$261 Roundtrip, found 6 days ago
$261
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, Oct 5 from Oakland to Chicago, returning Fri, Oct 9, priced at $261 found 6 days ago
Wed, Nov 4 - Sat, Nov 7
SMF
Sacramento
ORD
Chicago
$283 Roundtrip, found 10 hours ago
$283
Roundtrip
found 10 hours ago
Select Delta flight, departing Wed, Nov 4 from Sacramento to Chicago, returning Sat, Nov 7, priced at $283 found 10 hours ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Chicago Hotel Collection River North
3.0-star property

The Chicago Hotel Collection River North

7.4/10 Good! (798 reviews)

Oct 14 - Oct 17

3 night stay

Sacramento (SMF) to Chicago (ORD)

Delta • Non-stop roundtrip • Coach
Price was $692, price is now $556 per person
$556
per person
just found
I booked a premium room with 1 Queen and 1 1 double sofa bed”. When we arrived to the lobby it was empty except for three guys drinking alcohol out of paper bags and vaping directly across from the check in desk. That was my first sign this may not be the right place for me and my daughter. Then we get to the room. The “double sofa bed” was a dirty, stained (with what looked like blood) small leather sofa. This was in no way a double sofa bed. We then looked out the window where our view was disgusting piles of trash and dirty stained sheets. I could not stay there. I didn’t feel safe. We left immediately after explaining to Expedia the issue. I had to book another hotel and Expedia has refused to refund my money despite selling me something I did not get.

Reviewed on Sep 4, 2026

Chicago Marriott Downtown Magnificent Mile
4.0-star property

Chicago Marriott Downtown Magnificent Mile

8.8/10 Excellent! (1,013 reviews)

Oct 14 - Oct 17

3 night stay

Sacramento (SMF) to Chicago (ORD)

Delta • Non-stop roundtrip • Coach
Price was $949, price is now $687 per person
$687
per person
just found
Great!

Reviewed on Sep 4, 2026

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (5,106 reviews)

Oct 31 - Nov 3

3 night stay

Oakland (OAK) to Chicago (ORD)

Alaska Airlines • Non-stop roundtrip • Coach
Price was $847, price is now $591 per person
$591
per person
found 17 hours ago
Great food, wonderful sky bar. Excellent stay

Reviewed on Sep 5, 2026

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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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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.

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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.