$43 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.

Fri, Aug 8 - Sun, Aug 10
SMF
Sacramento Intl.
ORD
O'Hare Intl.
$301 Roundtrip, found 3 hours ago
$301
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, Aug 8 from Sacramento Intl. to O'Hare Intl., returning Sun, Aug 10, priced at $301 found 3 hours ago
Fri, Aug 8 - Sat, Aug 23
OAK
Oakland Intl.
ORD
O'Hare Intl.
$403 Roundtrip, found 1 day ago
$403
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, Aug 8 from Oakland Intl. to O'Hare Intl., returning Sat, Aug 23, priced at $403 found 1 day ago
Fri, Aug 8 - Mon, Aug 11
OAK
Oakland Intl.
MDW
Midway Intl.
$504 Roundtrip, found 6 days ago
$504
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Aug 8 from Oakland Intl. to Midway Intl., returning Mon, Aug 11, priced at $504 found 6 days ago
Sat, Aug 9 - Tue, Aug 12
SMF
Sacramento Intl.
MDW
Midway Intl.
$563 Roundtrip, found 1 day ago
$563
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Aug 9 from Sacramento Intl. to Midway Intl., returning Tue, Aug 12, priced at $563 found 1 day ago

Airfares from $43 One Way, $86 Round Trip from Modesto to Chicago

Prices starting at $86 for return flights and $43 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 6 - Sat, Sep 13
SMF
Sacramento
ORD
Chicago
$86 Roundtrip, just found
$86
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Sep 6 from Sacramento to Chicago, returning Sat, Sep 13, priced at $86 just found
Wed, Sep 10 - Sat, Sep 13
OAK
Oakland
ORD
Chicago
$106 Roundtrip, found 4 hours ago
$106
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Wed, Sep 10 from Oakland to Chicago, returning Sat, Sep 13, priced at $106 found 4 hours ago
Wed, Oct 22 - Sat, Oct 25
OAK
Oakland
MDW
Chicago
$141 Roundtrip, just found
$141
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Oct 22 from Oakland to Chicago, returning Sat, Oct 25, priced at $141 just found
Wed, Oct 22 - Sat, Oct 25
OAK
Oakland
MDW
Chicago
$179 Roundtrip, just found
$179
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Oct 22 from Oakland to Chicago, returning Sat, Oct 25, priced at $179 just found
Sat, Nov 1 - Wed, Nov 5
OAK
Oakland
ORD
Chicago
$217 Roundtrip, found 4 days ago
$217
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Sat, Nov 1 from Oakland to Chicago, returning Wed, Nov 5, priced at $217 found 4 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile
3.0-star property

Courtyard by Marriott Chicago Magnificent Mile

8.8/10 Excellent! (1,460 reviews)

Sep 4 - Sep 8

4 night stay

Sacramento (SMF) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Sacramento (SMF)

Spirit Airlines • Coach
per person
found 1 day ago
I felt it was all so confusing there. The parking is horrendous. You get an email stating 45 a night for self park but it’s 65-this is directly from the hotel. I ordered my room through Orbitz. Don’t get insurance through Orbitz as the hotel charges insurance as well. Expect a hold fee for incidentals of 70 a night. The room was clean. But minor scuffs. I took photos to make sure a charge didn’t come back to me. Bus is the way to go as the city is overpriced on uber. Orbitz does not match the hotel price be aware. It would seem like my issue is with Orbitz but it’s the hotel with all the surprise fees. If you’re looking for a clean hotel this is it. If you’re looking for friendly staff this isn’t it. If you offer someone something like water then you should offer everyone, I work in property management and if I offered someone something and not the next it would be a problem. Just saying. The pool is small. And right next to the gym and on the 10th floor. We were on the 18th and it wasn’t bad but just ok. Would I stay again probably not. I am big on friendly staff. Park other places as you can find way cheaper. We stayed for 3 nights. 195 total. Photos attached are the day we left. I don’t play when it comes to picking up behind myself.

Reviewed on May 25, 2025

LondonHouse Chicago, Curio Collection by Hilton
4.5-star property

LondonHouse Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (3,342 reviews)

Sep 3 - Sep 7

4 night stay

Sacramento (SMF) to Chicago (ORD)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Unbelievable property, great hospitality, clean, beautiful rooms, lots of amenities, and of course there is the rooftop. I like that they allow guests to have priority on the rooftop in terms of going up there. We will be back for sure. Thank you, London house.!

Reviewed on Jun 15, 2025

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,000 reviews)

Sep 4 - Sep 8

4 night stay

Sacramento (SMF) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.

Reviewed on Sep 13, 2024

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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.

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.