$75 Cheap flight deals from Chicago (CHI) to Oceanside (SAN)

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This Weekend's Flight Deals from Chicago to Oceanside

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, Mar 21 - Sat, Mar 28
MDW
Midway Intl.
SAN
San Diego Intl.
$574 Roundtrip, found 7 hours ago
$574
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sat, Mar 21 from Midway Intl. to San Diego Intl., returning Sat, Mar 28, priced at $574 found 7 hours ago
Sat, Mar 21 - Sat, Mar 28
ORD
O'Hare Intl.
SAN
San Diego Intl.
$619 Roundtrip, found 1 hour ago
$619
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Sat, Mar 21 from O'Hare Intl. to San Diego Intl., returning Sat, Mar 28, priced at $619 found 1 hour ago
Sun, Mar 22 - Tue, Mar 24
ORD
O'Hare Intl.
CLD
McClellan-Palomar
$644 Roundtrip, found 1 day ago
$644
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Mar 22 from O'Hare Intl. to McClellan-Palomar, returning Tue, Mar 24, priced at $644 found 1 day ago
Fri, Mar 20 - Wed, Mar 25
RFD
Greater Rockford
SAN
San Diego Intl.
$725 Roundtrip, found 1 day ago
$725
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Mar 20 from Greater Rockford to San Diego Intl., returning Wed, Mar 25, priced at $725 found 1 day ago

Airfares from $75 One Way, $152 Round Trip from Chicago to Oceanside

Prices starting at $152 for return flights and $75 for one-way flights to Oceanside 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, Apr 22 - Wed, Apr 29
ORD
Chicago
SAN
San Diego
$152 Roundtrip, found 5 days ago
$152
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Wed, Apr 22 from Chicago to San Diego, returning Wed, Apr 29, priced at $152 found 5 days ago
Wed, Apr 22 - Sat, Apr 25
MDW
Chicago
SAN
San Diego
$160 Roundtrip, found 6 days ago
$160
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Apr 22 from Chicago to San Diego, returning Sat, Apr 25, priced at $160 found 6 days ago
Wed, Apr 22 - Sat, Apr 25
ORD
Chicago
SAN
San Diego
$176 Roundtrip, found 6 days ago
$176
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Apr 22 from Chicago to San Diego, returning Sat, Apr 25, priced at $176 found 6 days ago
Tue, May 12 - Sat, May 16
ORD
Chicago
SAN
San Diego
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select United flight, departing Tue, May 12 from Chicago to San Diego, returning Sat, May 16, priced at $197 found 5 days ago
Wed, Apr 22 - Sat, Apr 25
RFD
Rockford
SAN
San Diego
$201 Roundtrip, found 6 days ago
$201
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Apr 22 from Rockford to San Diego, returning Sat, Apr 25, priced at $201 found 6 days ago

Oceanside economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Beau Downtown San Diego Gaslamp Quar
3.0-star property

The Beau Downtown San Diego Gaslamp Quar

8.8/10 Excellent! (626 reviews)

May 10 - May 15

5 night stay

Chicago (CHI) to San Diego (SAN)

Southwest Airlines • Non-stop • Coach

San Diego (SAN) to Chicago (CHI)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $869, price is now $582 per person
$582
per person
found 1 day ago
overall, a nice stay. decor very spot on in keeping classic feel. Beautiful bar. Staffed with ABSOLUTELY lovely people! Only non-positives; no elevator, no fridge, portable AC unit.

Reviewed on Aug 28, 2025

The Sofia Hotel
3.5-star property

The Sofia Hotel

8.6/10 Excellent! (1,818 reviews)

Apr 17 - Apr 21

4 night stay

Chicago (CHI) to San Diego (SAN)

Southwest Airlines • Coach

San Diego (SAN) to Chicago (CHI)

American Airlines • Coach
Price was $1,889, price is now $837 per person
$837
per person
found 1 day ago
Beautiful historical hotel, amazing location a few minutes from the port, incredibly fast checkin, room had character and stay was perfect

Reviewed on Jan 5, 2026

Los Bungalows
2.5-star property

Los Bungalows

8.2/10 Very Good! (520 reviews)

Apr 18 - Apr 25

7 night stay

Chicago (ORD) to San Diego (SAN)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,309, price is now $895 per person
$895
per person
found 12 hours ago
Great stay as usual. I absolutely love staying here.

Reviewed on Nov 27, 2023

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Oceanside packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
The Sofia Hotel
3.5-star property

The Sofia Hotel

8.6/10 Excellent! (1,818 reviews)

Apr 30 - May 4

4 night stay

Chicago (ORD) to San Diego (SAN)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,076, price is now $816 per person
$816
per person
found 19 hours ago
Beautiful historical hotel, amazing location a few minutes from the port, incredibly fast checkin, room had character and stay was perfect

Reviewed on Jan 5, 2026

Margaritaville Hotel San Diego Gaslamp Quarter
4.0-star property

Margaritaville Hotel San Diego Gaslamp Quarter

9/10 Wonderful! (1,259 reviews)

Apr 30 - May 4

4 night stay

Chicago (ORD) to San Diego (SAN)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,333, price is now $1,012 per person
$1,012
per person
found 19 hours ago
We were able to check in early and check out late, but of course had to pay a fee

Reviewed on Oct 3, 2025

The Beau Downtown San Diego Gaslamp Quar
3.0-star property

The Beau Downtown San Diego Gaslamp Quar

8.8/10 Excellent! (626 reviews)

Apr 30 - May 4

4 night stay

Chicago (ORD) to San Diego (SAN)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,270, price is now $1,027 per person
$1,027
per person
found 19 hours ago
overall, a nice stay. decor very spot on in keeping classic feel. Beautiful bar. Staffed with ABSOLUTELY lovely people! Only non-positives; no elevator, no fridge, portable AC unit.

Reviewed on Aug 28, 2025

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More About Flying To Oceanside from Chicago

Route Information for Flights from Chicago to Oceanside

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

Chicago to Oceanside

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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.