$67 Cheap flight deals from Chicago (CHI) to El Cajon (SAN)
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This Weekend's Flight Deals from Chicago to El Cajon
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.
MDW
Midway Intl.
SAN
San Diego Intl.
$299 Roundtrip, found 2 hours ago
$299
Roundtrip
found 2 hours ago
ORD
O'Hare Intl.
CLD
McClellan-Palomar
$580 Roundtrip, found 2 days ago
$580
Roundtrip
found 2 days ago
ORD
O'Hare Intl.
CLD
McClellan-Palomar
$580 Roundtrip, found 2 days ago
$580
Roundtrip
found 2 days ago
Airfares from $67 One Way, $156 Round Trip from Chicago to El Cajon
Prices starting at $156 for return flights and $67 for one-way flights to El Cajon were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
Chicago
SAN
San Diego
$156 Roundtrip, found 1 day ago
$156
Roundtrip
found 1 day ago
ORD
Chicago
SAN
San Diego
$156 Roundtrip, found 23 hours ago
$156
Roundtrip
found 23 hours ago
RFD
Rockford
SAN
San Diego
$157 Roundtrip, found 6 days ago
$157
Roundtrip
found 6 days ago
ORD
Chicago
SAN
San Diego
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
ORD
Chicago
SAN
San Diego
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
El Cajon economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
The Beau Downtown San Diego Gaslamp Quar
8.8/10 Excellent! (535 reviews)
Feb 7 - Feb 11
4 night stay
Chicago (CHI) to San Diego (SAN)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $807, price is now $567 per person
$567
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
3.5-star property
The Sofia Hotel
8.4/10 Very Good! (1,627 reviews)
Feb 7 - Feb 11
4 night stay
Chicago (CHI) to San Diego (SAN)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $967, price is now $582 per person
$582
per person
found 1 day ago
The hotel was well staffed and the rooms where clean.
Reviewed on Apr 14, 2025
3.0-star property
Coronado Beach Resort
9/10 Wonderful! (742 reviews)
Feb 2 - Feb 6
4 night stay
Chicago (CHI) to San Diego (SAN)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $845, price is now $571 per person
$571
per person
found 1 day ago
We had such a fabulous stay! I am so glad we stayed here versus the hotel del Coronado. The staff was so friendly, the one bedroom so spacious with a kitchen, such fabulous amenities that we used their bikes to bike around the island, hot tub, and the location is unbeatable. A great deal for the price we were so so happy here!
Reviewed on Apr 7, 2024
El Cajon packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Beach Terrace
9.4/10 Exceptional! (1,003 reviews)
Jan 31 - Feb 4
4 night stay
Chicago (ORD) to San Diego (SAN)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,380, price is now $1,101 per person
$1,101
per person
found 15 hours ago
Fantastic! I love that it's right on the beach. Chairs, towels, umbrellas, beach toys and boogie boards available. Staff came around with ice cream, nice touch! Loved sitting at the fire pits at night.
Reviewed on Jul 9, 2025
5.0-star property
Shore House at The Del, LXR Hotels & Resorts
9.2/10 Wonderful! (109 reviews)
Feb 18 - Feb 21
3 night stay
Chicago (ORD) to San Diego (SAN)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $2,028, price is now $1,594 per person
$1,594
per person
found 1 day ago
Very nice and right on the beach!
Reviewed on Jul 22, 2024
5.0-star property
Beach Village at The Del, LXR Hotels & Resorts
9.2/10 Wonderful! (118 reviews)
Feb 18 - Feb 21
3 night stay
Chicago (ORD) to San Diego (SAN)
Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,958, price is now $2,472 per person
$2,472
per person
found 1 day ago
El Cajon first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
WorldMark San Diego - Mission Valley
8.4/10 Very Good! (259 reviews)
Feb 13 - Feb 16
3 night stay
Chicago (ORD) to San Diego (SAN)
American Airlines • Non-stop • FirstClass
San Diego (SAN) to Chicago (ORD)
Alaska Airlines • Non-stop • FirstClass
Price was $1,350, price is now $1,216 per person
$1,216
per person
found 23 hours ago
Location was perfect
Reviewed on Oct 22, 2024
4.0-star property
Omni San Diego Hotel at the Ballpark
9.2/10 Wonderful! (2,046 reviews)
Feb 13 - Feb 16
3 night stay
Chicago (ORD) to San Diego (SAN)
American Airlines • Non-stop • FirstClass
San Diego (SAN) to Chicago (ORD)
Alaska Airlines • Non-stop • FirstClass
Price was $1,516, price is now $1,360 per person
$1,360
per person
found 23 hours ago
My wife and I loved this hotel. The location was ideal for Gaslamp fun and even better for going to a Padres game because there is direct access to the ballpark for hotel guests. The room was fantastic, clean, and smelled great. Vibes at the pool were great. Loved the coffee at Fres.co, drinks at Ace Porter, and the Tiki Social poolside pop-up at Tortuga was off the charts. Excellent service, too. A perfect home base for our first visit to San Diego -- and hopefully our next visit, too. Just one request: Put a chair on the balcony. :)
Reviewed on Jul 19, 2025
4.0-star property
InterContinental San Diego by IHG
9.2/10 Wonderful! (1,080 reviews)
Feb 13 - Feb 16
3 night stay
Chicago (ORD) to San Diego (SAN)
American Airlines • Non-stop • FirstClass
San Diego (SAN) to Chicago (ORD)
Alaska Airlines • Non-stop • FirstClass
Price was $1,550, price is now $1,394 per person
$1,394
per person
found 23 hours ago
Clean, well equipped rooms
Reviewed on Oct 13, 2025
More About Flying To El Cajon from Chicago
Route Information for Flights from Chicago to El Cajon
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | SAN |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to El Cajon
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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.