Nonstop Flights: Chicago to (Orlando $97) or (San Diego $139) r/t – United

[10/12/2019 @ 12:25 PM CT] Book this fare on: Priceline, BookingBuddy, Travelocity, SkyScanner, Expedia, Orbitz, Hotwire, CheapTickets.

The details on this page were accurate when this post was last updated (see time-stamp). Deals are usually valid 24 to 72 hours after posting, but can expire at any time. This website contains cookies for personalized ads and links to companies that may compensate this site when you click on their link. By continuing to use this website, you consent to the use of ads, affiliate links, and cookies.

United has round-trip flights from Chicago (ORD) to Orlando or San Diego (MCO/SAN) for $97-$139, NONSTOP. Flights October to February. No Holidays. Mostly on midweek, or weekdays.

Note: United “Basic Economy” fares do not include a free carry-on bag. Only a personal item (like a small laptop bag) is free. Seats are randomly assigned for free prior to boarding. If you have the United MileagePlus credit-card, use the “free checked bag” perk.

Note: The personal item size on United flights is smaller (9-in/10-in/17-in) than Frontier or Spirit (8-in/14-in/18-in).

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  • Orlando – Example Dates: (BookingBuddy / Priceline) Oct 22 – Oct 24 / Oct 22 – Oct 29 / Oct 28 – Oct 30 / Oct 28 – Oct 31 / Oct 28 – Nov 01 / Oct 28 – Nov 04 / Oct 29 – Oct 31 / Oct 29 – Nov 01 / Oct 29 – Nov 05 / Nov 04 – Nov 06 / Nov 04 – Nov 07 / Nov 05 – Nov 07 / Nov 06 – Nov 13 / Nov 11 – Nov 13 / Nov 11 – Nov 14 / Nov 11 – Nov 15 / Nov 11 – Nov 18 / Nov 12 – Nov 14 / Nov 12 – Nov 15 / Nov 12 – Nov 19 / Nov 13 – Nov 15 / Nov 13 – Nov 18 / Nov 13 – Nov 20 / Nov 16 – Nov 18 / Nov 16 – Nov 19 / Nov 16 – Nov 20 / Nov 16 – Nov 21 / Nov 17 – Nov 19 / Nov 17 – Nov 20 / Nov 17 – Nov 21 / Nov 18 – Nov 20 / Nov 18 – Nov 21 / Nov 18 – Nov 25 / Nov 19 – Nov 21 / Dec 10 – Dec 17 / Jan 11 – Jan 14 / Jan 11 – Jan 15 / Jan 11 – Jan 16 / Jan 13 – Jan 15 / Jan 13 – Jan 16 / Jan 14 – Jan 16 / Jan 27 – Jan 29 / Jan 27 – Jan 30 / Other dates: There are more dates available than the ones we list here, experiment on your own.
  • Orlando – Extended Weekend Dates: (BookingBuddy / Priceline) Nov 16 – Nov 18 / Nov 16 – Nov 19 / Jan 11 – Jan 14 / Other dates: There are more dates available than the ones we list here, experiment on your own.
  • San Diego – Example Dates: (BookingBuddy / Priceline) Oct 29 – Oct 31 / Oct 29 – Nov 01 / Oct 29 – Nov 02 / Oct 29 – Nov 05 / Oct 30 – Nov 01 / Oct 30 – Nov 02 / Nov 15 – Nov 19 / Nov 16 – Nov 19 / Nov 17 – Nov 19 / Dec 10 – Dec 15 / Jan 08 – Jan 11 / Jan 08 – Jan 13 / Jan 08 – Jan 15 / Jan 28 – Feb 01 / Jan 28 – Feb 04 / Jan 29 – Feb 01 / Jan 29 – Feb 05 / Feb 25 – Feb 29 / Feb 25 – Mar 03 / Other dates: There are more dates available than the ones we list here, experiment on your own.
  • San Diego – Extended Weekend Dates: (BookingBuddy / Priceline) Nov 15 – Nov 19 / Nov 16 – Nov 19 /Other dates: There are more dates available than the ones we list here, experiment on your own.
  • Before you finalize your purchase, do a quick check on BookingBuddy to see if any other site or airline is offering a better deal. Different booking websites will often have differing routes, prices, and availability.
  • If you want to see other deals that are still bookable you should check out the “Bookable Deals” page on our site. It filters out deals that have expired, or have low availability.

When you are ready to book your flight or hotel, please use the links on our site to begin your booking process so we receive credit for the referral.

I was able to pull this up on Priceline. Screenshot taken when this post was initially created. See timestamps at the top of this post.

Note: OTAs such as Travelocity and Priceline allow free cancellation without penalty within 24-hours after you purchase. As deals sell-out or expire quickly, this policy will allow you to “lock-in” the cheap fare while you sort out a plan. Just keep in mind that after 24-hours, you will not be able to cancel without the regular penalty.

Flight Details:




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  • [Cheap DFW] – Airfare and travel deals leaving from Dallas (DFW / DAL).

EXAM:ORD,MDW,MKE:MCO:UA*UA:0::e-:7,5,4,3,2:1440:106:DEBUG:avg127

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