$98 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.

Sun, Dec 7 - Sun, Dec 14
SMF
Sacramento Intl.
ORD
O'Hare Intl.
$245 Roundtrip, found 12 hours ago
$245
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sun, Dec 7 from Sacramento Intl. to O'Hare Intl., returning Sun, Dec 14, priced at $245 found 12 hours ago
Sun, Dec 7 - Sun, Dec 14
SMF
Sacramento Intl.
MDW
Midway Intl.
$276 Roundtrip, found 5 days ago
$276
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Dec 7 from Sacramento Intl. to Midway Intl., returning Sun, Dec 14, priced at $276 found 5 days ago
Sun, Dec 7 - Sat, Dec 13
OAK
Oakland Intl.
MDW
Midway Intl.
$456 Roundtrip, found 5 days ago
$456
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sun, Dec 7 from Oakland Intl. to Midway Intl., returning Sat, Dec 13, priced at $456 found 5 days ago
Fri, Dec 5 - Mon, Dec 8
OAK
Oakland Intl.
ORD
O'Hare Intl.
$476 Roundtrip, found 2 days ago
$476
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Fri, Dec 5 from Oakland Intl. to O'Hare Intl., returning Mon, Dec 8, priced at $476 found 2 days ago

Airfares from $98 One Way, $200 Round Trip from Modesto to Chicago

Prices starting at $200 for return flights and $98 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, Feb 21 - Sat, Feb 28
SMF
Sacramento
ORD
Chicago
$200 Roundtrip, found 3 hours ago
$200
Roundtrip
found 3 hours ago
Select Alaska Airlines flight, departing Sat, Feb 21 from Sacramento to Chicago, returning Sat, Feb 28, priced at $200 found 3 hours ago
Sat, Jan 31 - Thu, Feb 19
SMF
Sacramento
ORD
Chicago
$213 Roundtrip, found 6 days ago
$213
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jan 31 from Sacramento to Chicago, returning Thu, Feb 19, priced at $213 found 6 days ago
Tue, Jan 13 - Tue, Jan 20
OAK
Oakland
ORD
Chicago
$255 Roundtrip, found 5 days ago
$255
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Tue, Jan 13 from Oakland to Chicago, returning Tue, Jan 20, priced at $255 found 5 days ago
Tue, Jan 13 - Sun, Jan 18
OAK
Oakland
ORD
Chicago
$255 Roundtrip, found 5 days ago
$255
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jan 13 from Oakland to Chicago, returning Sun, Jan 18, priced at $255 found 5 days ago
Wed, Feb 18 - Sat, Feb 21
SMF
Sacramento
ORD
Chicago
$258 Roundtrip, found 4 days ago
$258
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Wed, Feb 18 from Sacramento to Chicago, returning Sat, Feb 21, priced at $258 found 4 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Hoxton Chicago
4.0-star property

The Hoxton Chicago

9/10 Wonderful! (1,001 reviews)

Dec 31 - Jan 5

5 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,032, price is now $692 per person
$692
per person
just found
awesome area and hotel

Reviewed on Sep 1, 2025

The Emily Hotel
4.0-star property

The Emily Hotel

9.2/10 Wonderful! (1,264 reviews)

Dec 31 - Jan 5

5 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,419, price is now $808 per person
$808
per person
found 4 hours ago
Cute and trendy hotwl but there was a loud party on-site which ruined experience. It felt clean but our mini fridge had takeout left from former guest, so maid service obviously missed that.

Reviewed on Jul 26, 2025

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (380 reviews)

Dec 31 - Jan 5

5 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,232, price is now $717 per person
$717
per person
found 4 hours 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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Earn Miles for Flights From 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.

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.