[06/21/2022 @ 02:16 PM CT] Book this fare on: Priceline, BookingBuddy, Travelocity, Tripadvisor, Skyscanner, Expedia, Orbitz, Hotwire, CheapTickets, Kayak.
[07/20/2022 @ 10:58 AM CT] This deal is still available, but the original date ranges may have shifted. We have updated the example date links in this post to reflect those changes. Expect prices to fluctuate by about +/- 10%.
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.
American Airlines and United have round-trip flights from Chicago (ORD) to Portland, Maine or Nashville (PWM, BNA) for $118-$128, NONSTOP. Flights between August and November.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Additional Savings: Sam’s Club is selling $500 Airbnb gift cards for $460 [linked]. You can save an additional $40 on your next Airbnb if you are spending more than $500 on the stay.
Booking a Flight+Hotel together as a package will usually be cheaper than booking each one separately. You can easily construct your own package deals on Expedia, Travelocity, and Priceline. The savings amount will vary depending on the combination of website, flight, and hotel, so be sure to compare the checkout prices on each site before purchase.
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- Chicago to Portland, Maine – Example Dates: (BookingBuddy / Priceline) Sep 13 – Sep 15 / Sep 13 – Sep 17 / Sep 17 – Sep 21 / Sep 17 – Sep 22 / Sep 17 – Sep 24 / Sep 19 – Sep 21 / Sep 19 – Sep 22 / Sep 20 – Sep 22 / Sep 20 – Sep 27 / Sep 26 – Sep 28 / Sep 28 – Oct 05 / Oct 04 – Oct 11 / Oct 12 – Oct 19 / Oct 18 – Oct 22 / Oct 19 – Oct 22 / Oct 19 – Oct 26 / Oct 22 – Oct 26 / Oct 22 – Oct 29 / Oct 25 – Oct 29 / Oct 26 – Oct 29 / Other dates: There are more dates available than the ones we list here, experiment on your own.
- Chicago to Nashville - Example Dates: (BookingBuddy / Priceline) Aug 16 - Aug 18 / Aug 16 - Aug 20 / Aug 16 - Aug 23 / Aug 17 - Aug 24 / Aug 20 - Aug 23 / Aug 20 - Aug 24 / Aug 20 - Aug 25 / Aug 20 - Aug 27 / Aug 23 - Aug 25 / Aug 23 - Aug 27 / Aug 23 - Aug 30 / Aug 24 - Aug 27 / Aug 24 - Aug 31 / Aug 27 - Aug 30 / Aug 27 - Aug 31 / Aug 29 - Aug 31 / Aug 30 - Sep 06 / Aug 31 - Sep 07 / Sep 03 - Sep 06 / Sep 03 - Sep 07 / Sep 03 - Sep 08 / Sep 03 - Sep 10 / Sep 07 - Sep 10 / Sep 07 - Sep 14 / Sep 10 - Sep 13 / Sep 10 - Sep 14 / Sep 10 - Sep 17 / Sep 12 - Sep 14 / Sep 12 - Sep 17 / Sep 13 - Sep 17 / Sep 13 - Sep 20 / Sep 14 - Sep 17 / Sep 14 - Sep 21 / Sep 17 - Sep 20 / Sep 17 - Sep 21 / Sep 17 - Sep 22 / Sep 17 - Sep 24 / Sep 20 - Sep 24 / Sep 20 - Sep 27 / Sep 24 - Sep 27 / Sep 24 - Sep 28 / Sep 26 - Sep 28 / Sep 26 - Oct 01 / Sep 27 - Oct 04 / Sep 28 - Oct 01 / Sep 28 - Oct 05 / Oct 01 - Oct 04 / Oct 01 - Oct 05 / Oct 03 - Oct 05 / Oct 04 - Oct 11 / Oct 05 - Oct 12 / Oct 08 - Oct 11 / Oct 08 - Oct 12 / Oct 08 - Oct 13 / Oct 10 - Oct 12 / Oct 10 - Oct 13 / Oct 11 - Oct 13 / Oct 11 - Oct 18 / Oct 12 - Oct 19 / Oct 18 - Oct 25 / Oct 19 - Oct 22 / Oct 19 - Oct 26 / Oct 22 - Oct 25 / Oct 22 - Oct 26 / Oct 22 - Oct 27 / Oct 22 - Oct 29 / Oct 24 - Oct 26 / Oct 24 - Oct 27 / Oct 25 - Oct 27 / Oct 25 - Oct 29 / Oct 25 - Nov 01 / Oct 26 - Oct 29 / Oct 26 - Nov 02 / Oct 29 - Nov 01 / Oct 29 - Nov 02 / Oct 29 - Nov 03 / Oct 29 - Nov 05 / Oct 31 - Nov 02 / Oct 31 - Nov 03 / Oct 31 - Nov 05 / Nov 01 - Nov 03 / Nov 01 - Nov 05 / Nov 02 - Nov 05 / Nov 03 - Nov 05 / Other dates: There are more dates available than the ones we list here, experiment on your own.
- Chicago to Nashville - Extended Weekend Dates: (BookingBuddy / Priceline) Aug 20 - Aug 23 / Aug 27 - Aug 30 / Sep 03 - Sep 06 / Sep 10 - Sep 13 / Sep 17 - Sep 20 / Sep 24 - Sep 27 / Oct 01 - Oct 04 / Oct 08 - Oct 11 / Oct 22 - Oct 25 / Oct 29 - Nov 01 / Other dates: There are more dates available than the ones we list here, experiment on your own.
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.
- Tips: Vacation rentals on Vrbo are usually cheaper per night for longer stays than shorter stays. This is due to three main factors; The first is that most properties have a cleaning fee that is a fixed rate, the second is that many hosts provide discounts for stays longer than 6-days, the third is that the Vrbo service fee percentage is higher on short stays.
- Tips: You can (and should) sort the Vrbo vacation rental search results by “Total” price. Doing so exposes properties with high fees. For example, a $140 per-night property with $100 fees will rank as being more expensive than a $150 per-night property with $30 fees, when sorted. Sorting by “most reviews” is also a good option, as this will show you the most popular properties.
- Tips: Rent a car for cheaper by using Priceline’s “Express Deals”. The rental car company will be hidden until after you purchase, but this allows those companies to undercut the published rate indirectly. You can remove low quality companies from those hidden results. The trick is to use the quality filter on their website to remove any rental car company with a review rating under 7.0 and then pick the deals that survive the filter.
- Tips: Use Tripadvisor to create a Hotel “short list”. First, plug in your dates and destination. Then select “Sort by Traveler Ranked”. Finally, select the “Traveler Ranking” filter to show “only 4* and up”. Use this resulting “short list” of hotels to find the cheapest one with a high ranking.
- Tips: Hotel rates for Weekend dates are usually higher than the rates for Sunday through Thursday. Tripadvisor has a color-coded date calendar, red when the average hotel price for that day is more expensive, green for less expensive. You can use this to get an overview of what dates in the month are at a discount.
- Tips: Different booking websites will often have differing routes, prices, and availability. Before you finalize your purchase, do a quick check on BookingBuddy, Skyscanner, and Kayak to see if any other site or airline is offering a better deal.
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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.
- 6-month moving average: $251
- Book this fare on: Priceline, BookingBuddy, Travelocity, Tripadvisor, Skyscanner, Expedia, Orbitz, Hotwire, CheapTickets, Kayak.
- Link to CheapTickets.com coupon code page – Check this page on Cheaptickets.com to save about 10% to 20% on your next Hotel or Package booking.
- Link to Travelocity coupon code page – Check this page on Travelocity to save about 10% to 20% on your next Hotel or Package booking.
- Link to Orbitz coupon code page – Check this page on Orbitz to save about 10% to 20% on your next Hotel or Package booking.
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- Airfare + hotel: Priceline, Travelocity, Expedia, Orbitz, Hotwire, CheapTickets.com, Skyscanner, Kayak
- Vacation rentals: Vrbo
- Airlines: Iberia, Hawaiian Airlines, Avianca, Lufthansa, Swiss, Qatar Airways, Emirates, KLM
- Hotel search: TripAdvisor, Hotels.com, HotelsCombined.com, Booking.com, Agoda
- Car rental: Priceline, Rentalcars.com
Flights departing from a different city:
- Flights from New York
- Flights from Chicago or Milwaukee
- Flights from Los Angeles (LAX, ONT, BUR, LGB, SNA)
- Flights from Seattle
- Flights from Portland, Oregon (PDX)
- Flights from Phoenix
- Flights from Denver
- Flights from Houston (via our website: Escape Houston)
- Flights from Austin or San Antonio (via our website: Escape ATX)
- Flights from Dallas (via our website: Cheap DFW)
Other Useful Links:
- [Budget Travel] – list all the posts that deal with Budget Travel (filter out all the flight deal posts)