Chicago to El Cajon Flights (CHI-SAN) from $50

Wander Wisely with exceptional service, 24/7 support

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Selected fares from Chicago to El Cajon

The cheapest prices found with in the last 7 days for return flights were $100 and $50 for one-way flights to El Cajon for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Jun 4 - Tue, Jun 11
ORD
O'Hare Intl.
SAN
San Diego Intl.
$100 Roundtrip, found 2 hours ago
$100
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Jun 4 from O'Hare Intl. to San Diego Intl., returning Tue, Jun 11, priced at $100 found 2 hours ago
Frontier Airlines
Sat, May 18 - Wed, May 22
MDW
Midway Intl.
SAN
San Diego Intl.
$139 Roundtrip, found 5 days ago
$139
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 18 from Midway Intl. to San Diego Intl., returning Wed, May 22, priced at $139 found 5 days ago
Alaska Airlines
Tue, Jul 16 - Tue, Jul 23
ORD
O'Hare Intl.
SAN
San Diego Intl.
$314 Roundtrip, found 21 hours ago
$314
Roundtrip
found 21 hours ago
Select Alaska Airlines flight, departing Tue, Jul 16 from O'Hare Intl. to San Diego Intl., returning Tue, Jul 23, priced at $314 found 21 hours ago

Save more with El Cajon Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Sofia Hotel

The Sofia Hotel

3.5 out of 5
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
Chicago (MDW) to San Diego (SAN)
Paradise Point Resort & Spa

Paradise Point Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
Chicago (MDW) to San Diego (SAN)
The Wayfarer San Diego

The Wayfarer San Diego

4 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
Chicago (MDW) to San Diego (SAN)
The Lodge at Torrey Pines

The Lodge at Torrey Pines

5 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
Chicago (MDW) to San Diego (SAN)
Pacific Terrace Hotel

Pacific Terrace Hotel

4 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
Chicago (MDW) to San Diego (SAN)
Ocean Park Inn

Ocean Park Inn

3 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 5
Roundtrip non-stop flight included
Chicago (MDW) to San Diego (SAN)
Don't see what you're looking for?
See all available trips from Chicago to El Cajon
View all trips