$96 Cheap flight deals from Carlsbad (SAN) to Chicago (CHI)

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This Weekend's Flight Deals from Carlsbad 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, Oct 10 - Sun, Oct 11
SAN
San Diego Intl.
ORD
O'Hare Intl.
$383 Roundtrip, found 1 hour ago
$383
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Oct 10 from San Diego Intl. to O'Hare Intl., returning Sun, Oct 11, priced at $383 found 1 hour ago
Fri, Oct 9 - Sat, Oct 10
CLD
McClellan-Palomar
ORD
O'Hare Intl.
$438 Roundtrip, found 6 days ago
$438
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Oct 9 from McClellan-Palomar to O'Hare Intl., returning Sat, Oct 10, priced at $438 found 6 days ago
Sat, Oct 10 - Tue, Oct 13
SAN
San Diego Intl.
MDW
Midway Intl.
$567 Roundtrip, found 4 hours ago
$567
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Oct 10 from San Diego Intl. to Midway Intl., returning Tue, Oct 13, priced at $567 found 4 hours ago

Airfares from $96 One Way, $143 Round Trip from Carlsbad to Chicago

Prices starting at $143 for return flights and $96 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, Nov 11 - Tue, Nov 17
SAN
San Diego
ORD
Chicago
$143 Roundtrip, found 21 hours ago
$143
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Wed, Nov 11 from San Diego to Chicago, returning Tue, Nov 17, priced at $143 found 21 hours ago
Thu, Oct 29 - Wed, Nov 4
SAN
San Diego
ORD
Chicago
$163 Roundtrip, found 22 hours ago
$163
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Thu, Oct 29 from San Diego to Chicago, returning Wed, Nov 4, priced at $163 found 22 hours ago
Tue, Oct 20 - Sat, Oct 31
SAN
San Diego
MDW
Chicago
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Oct 20 from San Diego to Chicago, returning Sat, Oct 31, priced at $257 found 2 days ago
Tue, Oct 20 - Sat, Oct 31
SAN
San Diego
ORD
Chicago
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Select United flight, departing Tue, Oct 20 from San Diego to Chicago, returning Sat, Oct 31, priced at $257 found 2 days ago
Tue, Oct 20 - Sat, Oct 31
SAN
San Diego
ORD
Chicago
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Oct 20 from San Diego to Chicago, returning Sat, Oct 31, priced at $257 found 2 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

9.2/10 Wonderful! (527 reviews)

Nov 8 - Nov 11

3 night stay

San Diego (SAN) to Chicago (ORD)

Alaska Airlines • Roundtrip • Coach
Price was $943, price is now $693 per person
$693
per person
found 5 hours ago
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.

Reviewed on Sep 27, 2026

Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

9.2/10 Wonderful! (573 reviews)

Nov 27 - Dec 1

4 night stay

San Diego (SAN) to Chicago (ORD)

Alaska Airlines • Roundtrip • Coach
Price was $1,046, price is now $730 per person
$730
per person
found 20 hours ago

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (5,340 reviews)

Nov 13 - Nov 16

3 night stay

San Diego (SAN) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to San Diego (SAN)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,133, price is now $805 per person
$805
per person
found 1 day ago
We loved our stay at RIU. The hotel was walkable to Navy Pier and several great restaurants and shops. The only complaint I can think of is the bathroom door not shutting completely unless it was locked (made your shower chilly). We would definitely stay here again!

Reviewed on Oct 2, 2026

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More About Flying To Chicago from Carlsbad

Route Information for Flights from Carlsbad to Chicago

Origin Airport IATA Code
SAN
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Carlsbad to Chicago

Getting a spectacularly low fare on Carlsbad to Chicago flights is always possible when you use Orbitz as your personal travel planner. Orbitz is your essential travel resource for low cost flights from Carlsbad to Chicago, discount hotel accommodations, cheap car rentals, and more.

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Stay in Your Budget and Still Get Great Accommodations

Orbitz shoppers can access affordable vacation packages and have the option of booking their departure and arrival flights through different airlines, making travel less costly and more convenient. The best prices on flights from Carlsbad to Chicagoare always found on Orbitz.

Frequently asked questions

Are there non-stop flights from Carlsbad to Chicago?
You're in luck — there are 3 airlines which offer direct services from SAN to ORD. Here are some of the best:

  • United Airlines
  • American Airlines
  • Spirit Airlines

What is the shortest flight from Carlsbad to Chicago?
The quickest flight time from Carlsbad to Chicago is 3 hours and 51 minutes, which gives you plenty of time to indulge in a tipple or get engrossed in a book.
What airlines fly from Carlsbad to Chicago most frequently?
There are a couple of airlines offering frequent flights from San Diego Airport to O'Hare Airport, including United Airlines (UA). A top pick for many travelers, it operates 147 flights on this route every month. American Airlines (AA) will also take you to your destination in comfort. Offering 108 flights every month between Carlsbad and Chicago, it's another popular airline to look into.
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.