Cheap flight deals from Chicago (CHI) to Orland (CIC)

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Orland economy flight packages

Price found within the past 48 hours. Click for updated prices.
Encore Inn Inglewood
2.5-star property

Encore Inn Inglewood

6.4/10 (173 reviews)

Sep 5 - Sep 7

2 night stay

Chicago (CHI) to Los Angeles (LAX)

American Airlines • Roundtrip • Coach
Price was $590, price is now $283 per person
$283
per person
found 1 day ago
Very nasty looking not up to part .and they tried to get more money out of me

Reviewed on Jul 7, 2026

The Sofia Hotel
3.5-star property

The Sofia Hotel

8.6/10 Excellent! (2,321 reviews)

Aug 22 - Aug 29

7 night stay

Chicago (CHI) to San Diego (SAN)

United • Roundtrip • Coach
Price was $1,857, price is now $686 per person
$686
per person
found 1 day ago
We enjoyed our overnight at the Sofia. We arrived around 2pm and were able to get our room right away. The room was a bit small, but was stylish and comfortable. We were too early to try out the dinner menu at the restaurant Truvo (Mediterranean style) unfortunately, but had a lovely breakfast there the following day. Guests get a discount. The front desk staff member was also able to give us an additional hour at check out when we asked. The venue was centrally located and very walkable to places and events. We went to a baseball game (Padres won!) and visited the Navy Seal Museum which is very good and more interactive than we anticipated. We will go again and bring the grandchildren. Our only chagrin was that the air conditioning was louder than we’d have liked and blew onto the bed. I would advise wearing an eye mask so that it doesn’t blow onto the eyes.

Reviewed on Jul 10, 2026

Claremont Resort & Club
5.0-star property

Claremont Resort & Club

9/10 Wonderful! (1,028 reviews)

Aug 16 - Aug 21

5 night stay

Chicago (ORD) to Oakland (OAK)

American Airlines • Coach

Oakland (OAK) to Chicago (ORD)

Alaska Airlines • Coach
Save 100% on your flight
Price was $2,268, price is now $1,259 per person
$1,259
per person
found 1 day ago
Parking is a bit pricey and it would be nice if there was at least a discount for overnight guests. Appreciate that there are plenty of water fountains to fill your own bottle with filtered water. Room was clean and very pretty, bathroom was humongous. Pool area was well maintained but there were not enough sun chairs for everyone on Saturday afternoon. This is the perfect little resort to come for a whole family wellness trip to swim, exercise and eat well.

Reviewed on Jul 11, 2026

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Orland first class flight packages

Price found within the past 48 hours. Click for updated prices.
Villa Graziadio Executive Center at Pepperdine University
2.5-star property

Villa Graziadio Executive Center at Pepperdine University

9/10 Wonderful! (211 reviews)

Aug 13 - Aug 17

4 night stay

Chicago (CHI) to Los Angeles (LAX)

Delta • Non-stop roundtrip • FirstClass
Price was $1,573, price is now $1,271 per person
$1,271
per person
found 1 day ago
The location is very convenient and the views were awesome. The room was also very clean and quiet. Our only problem was with the extremely unhelpful staff member who couldn’t even tell us if our room came with a refrigerator or not. We had called ahead of time to find out this information and she simply said that she was new and it would stay on our reservation. We told her we booked through Expedia and she told us to simply go to the website and look it up there. How are we supposed to go look at a particular room type and what amenities it comes with when we already booked the room? It only shows what’s available for that particular night so it would not be a good place to go to. She could’ve at least said that she’d find out from someone else but she said she would have to hang up because she had other calls coming in. We also wanted to find out whether the cafeteria was open for the very next day and she didn’t have any information on that either but at least she said that she would find out and she had that information ready by the time we checked in.

Reviewed on Jul 5, 2026

Hotel Erwin Venice Beach
4.0-star property

Hotel Erwin Venice Beach

9/10 Wonderful! (1,004 reviews)

Aug 13 - Aug 17

4 night stay

Chicago (CHI) to Los Angeles (LAX)

Delta • Non-stop roundtrip • FirstClass
Price was $1,984, price is now $1,642 per person
$1,642
per person
found 1 day ago
It was good

Reviewed on Jul 9, 2026

Loews Hollywood Hotel
4.0-star property

Loews Hollywood Hotel

9.2/10 Wonderful! (5,304 reviews)

Aug 13 - Aug 17

4 night stay

Chicago (CHI) to Los Angeles (LAX)

Delta • Non-stop roundtrip • FirstClass
Price was $1,633, price is now $1,437 per person
$1,437
per person
found 1 day ago
It was not worth the price it needs some major zest to be charging $500 plus a night. The rooms did not look like the pictures

Reviewed on Jul 11, 2026

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More About Flying To Orland from Chicago

Route Information for Flights from Chicago to Orland

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

Chicago to Orland

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