$66 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.

Sun, May 18 - Sat, May 24
SAN
San Diego Intl.
MDW
Midway Intl.
$215 Roundtrip, found 2 days ago
$215
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, May 18 from San Diego Intl. to Midway Intl., returning Sat, May 24, priced at $215 found 2 days ago
Sat, May 17 - Mon, May 19
SAN
San Diego Intl.
ORD
O'Hare Intl.
$226 Roundtrip, just found
$226
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, May 17 from San Diego Intl. to O'Hare Intl., returning Mon, May 19, priced at $226 just found
Sun, May 18 - Thu, May 22
CLD
McClellan-Palomar
ORD
O'Hare Intl.
$558 Roundtrip, found 2 days ago
$558
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sun, May 18 from McClellan-Palomar to O'Hare Intl., returning Thu, May 22, priced at $558 found 2 days ago

Airfares from $66 One Way, $86 Round Trip from Carlsbad to Chicago

Prices starting at $86 for return flights and $66 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.

Thu, May 22 - Mon, Jun 2
SAN
San Diego
ORD
Chicago
$86 Roundtrip, found 15 hours ago
$86
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Thu, May 22 from San Diego to Chicago, returning Mon, Jun 2, priced at $86 found 15 hours ago
Wed, Jul 9 - Sat, Jul 12
SAN
San Diego
ORD
Chicago
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jul 9 from San Diego to Chicago, returning Sat, Jul 12, priced at $132 found 1 day ago
Sun, May 25 - Thu, May 29
SAN
San Diego
MDW
Chicago
$162 Roundtrip, found 1 day ago
$162
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, May 25 from San Diego to Chicago, returning Thu, May 29, priced at $162 found 1 day ago
Sat, Jul 26 - Sat, Aug 2
SAN
San Diego
ORD
Chicago
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jul 26 from San Diego to Chicago, returning Sat, Aug 2, priced at $163 found 1 day ago
Sat, Jul 26 - Sat, Aug 2
SAN
San Diego
ORD
Chicago
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jul 26 from San Diego to Chicago, returning Sat, Aug 2, priced at $163 found 1 day ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
InterContinental Chicago Magnificent Mile by IHG
4.5-star property

InterContinental Chicago Magnificent Mile by IHG

9/10 Wonderful! (1,798 reviews)

Jun 27 - Jun 30

3 night stay

San Diego (SAN) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
per person
found 1 day ago
The location was perfect, we were able to do all that we had planned to over the course of the two days, and we enjoyed how walkable the area was.

Reviewed on Mar 5, 2025

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

8.8/10 Excellent! (1,988 reviews)

Jun 27 - Jun 30

3 night stay

San Diego (SAN) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
per person
found 1 day ago
Had an amazing stay beautiful hotel

Reviewed on Feb 16, 2025

Arlo Chicago
4.0-star property

Arlo Chicago

9.2/10 Wonderful! (1,665 reviews)

Jun 27 - Jun 30

3 night stay

San Diego (SAN) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
per person
found 1 day ago
Nice hotel. Great location. Nice room. Pictures made hotel seem like it was so much more. It was just one small hallway. Nothing more. Very disappointed with the lobby. I thought by the pictures I was getting so much more! Payed a $150 resort fee for two night. There was absolutely no resort and no resort benefits. That was purely a money grab. Didn’t even get my room cleaned each day. Nice room. Nice hotel. Just less that I thought!

Reviewed on Oct 13, 2024

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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

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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.

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.