$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, Jul 18 - Wed, Jul 22
SMF
Sacramento Intl.
ORD
O'Hare Intl.
$367 Roundtrip, found 1 day ago
$367
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, Jul 18 from Sacramento Intl. to O'Hare Intl., returning Wed, Jul 22, priced at $367 found 1 day ago
Sat, Jul 18 - Tue, Jul 21
OAK
Oakland Intl.
ORD
O'Hare Intl.
$471 Roundtrip, found 15 hours ago
$471
Roundtrip
found 15 hours ago
Select Bargain Flight flight, departing Sat, Jul 18 from Oakland Intl. to O'Hare Intl., returning Tue, Jul 21, priced at $471 found 15 hours ago
Sat, Jul 18 - Wed, Jul 22
SMF
Sacramento Intl.
MDW
Midway Intl.
$530 Roundtrip, found 1 day ago
$530
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Jul 18 from Sacramento Intl. to Midway Intl., returning Wed, Jul 22, priced at $530 found 1 day ago
Sat, Jul 18 - Tue, Jul 21
OAK
Oakland Intl.
MDW
Midway Intl.
$554 Roundtrip, found 15 hours ago
$554
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Sat, Jul 18 from Oakland Intl. to Midway Intl., returning Tue, Jul 21, priced at $554 found 15 hours ago

Airfares from $117 One Way, $219 Round Trip from Modesto to Chicago

Prices starting at $219 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.

Sat, Sep 12 - Mon, Sep 14
OAK
Oakland
MDW
Chicago
$219 Roundtrip, found 5 days ago
$219
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Sep 12 from Oakland to Chicago, returning Mon, Sep 14, priced at $219 found 5 days ago
Sat, Sep 26 - Thu, Oct 1
SMF
Sacramento
ORD
Chicago
$240 Roundtrip, found 8 hours ago
$240
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Sep 26 from Sacramento to Chicago, returning Thu, Oct 1, priced at $240 found 8 hours ago
Thu, Sep 24 - Mon, Sep 28
OAK
Oakland
ORD
Chicago
$254 Roundtrip, found 14 hours ago
$254
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Thu, Sep 24 from Oakland to Chicago, returning Mon, Sep 28, priced at $254 found 14 hours ago
Wed, Aug 26 - Tue, Sep 1
OAK
Oakland
ORD
Chicago
$257 Roundtrip, found 7 hours ago
$257
Roundtrip
found 7 hours ago
Select Alaska Airlines flight, departing Wed, Aug 26 from Oakland to Chicago, returning Tue, Sep 1, priced at $257 found 7 hours ago
Sat, Aug 15 - Mon, Aug 17
SMF
Sacramento
MDW
Chicago
$261 Roundtrip, found 6 days ago
$261
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Aug 15 from Sacramento to Chicago, returning Mon, Aug 17, priced at $261 found 6 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (497 reviews)

Sep 3 - Sep 6

3 night stay

Sacramento (SMF) to Chicago (ORD)

Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,383, price is now $975 per person
$975
per person
found 1 day ago
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.

Reviewed on Jul 14, 2026

Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

9.2/10 Wonderful! (512 reviews)

Sep 2 - Sep 6

4 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,456, price is now $1,008 per person
$1,008
per person
found 12 hours ago

Level Chicago - River North
4.0-star property

Level Chicago - River North

9.2/10 Wonderful! (1,020 reviews)

Aug 21 - Aug 26

5 night stay

Sacramento (SMF) to Chicago (ORD)

United • Coach

Chicago (ORD) to Sacramento (SMF)

American Airlines • Coach
Price was $1,916, price is now $1,360 per person
$1,360
per person
found 1 day ago
This place was awesome. My son and I stayed here and it was a huge part of our trip to Chicago going well. Perfectly located by everything but not in the bustle of Michigan Ave. Still close to all the good food and museums. The pool, the lounges, the sauna, were perfect after museum and city days. All in all it was excellent. Highly recommend. The staff was also kinder and more helpful than I I’ve experienced in probably 5 years. Thank you Level River North.

Reviewed on Jul 15, 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

Find fantastic fares on domestic and international flights that suit your travel requirements and budget needs by heading to Orbitz. Orbitz has your cheap air tickets for flights from Modesto to Chicago.

Flights from Modesto to Chicago at bargain prices

Budgeting and hidden costs should be the least of your concerns when planning a trip. Your priority should be planning all the things you want to do during your stay. With our low fares on Modesto to Chicago flights, you know you are getting the best deal for your vacation or business trip budget—and not incurring hidden costs or paying for over-priced tickets offered by some airlines. We want to help you enjoy your trip the way you deserve.

Remain up-to-date on your flights from Modesto to Chicago

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Orbitz booking discounts for Modesto to Chicago flights

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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.