Category: <span>Bookable Chicago</span>

This fare requires an overnight connection in Lisbon on the return flight.

Tap Air Portugal has round-trip flights from Chicago (ORD) to Tenerife (TFS) for $205-$241 with a connection. Flights February to June. No Tuesday departures. Origin/Destination reversible.

Carry on bag with a maximum weight of 17.6 lbs is allowed for free on TAP. You can avoid seat selection fees by accepting the randomly assigned seat at the gate.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Patreon supporters receive a recap of all the airfare deals currently available everyday.

We don’t charge a subscription fee. Our deal notifications are available for FREE via Instagram, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

Click for more details and booking links Cheap Flights: Chicago to/from Canary Islands (Tenerife) $205-$241 r/t [February-June] – Tap Air Portugal

Airfare Deals Bookable Chicago Bookable Deals Flights from Chicago / Milwaukee TAP Air Portugal Tenerife

American Airlines has round-trip flights from Chicago (ORD) to Honolulu (HNL) for $282-$295 with a connection. Flights December to February. No Weekends. Departures on Monday, Tuesday, Wednesday, and Thursday.

Fare has a long (4-to-5-hour connection). Shorter connections are available for $313-$368.

You do not need to quarantine if you have a negative PCR COVID test. American Airlines has been directing their Hawaii customers to the LetsGetChecked at-home kit for $119 (linked).

Change fees are waived and carry-on bag is allowed for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Patreon supporters receive a recap of all the airfare deals currently available everyday.

We don’t charge a subscription fee. Our deal notifications are available for FREE via Instagram, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

Click for more details and booking links Cheap Flights: Chicago to Honolulu or Maui, Hawaii $282-$295 r/t [December-February] – American Airlines

Airfare Deals American Airlines Bookable Chicago Bookable Deals Flights from Chicago / Milwaukee Honolulu Oneworld

American Airlines and Alaska Airlines have round-trip flights from Los Angeles (LAX) to Chicago (ORD) for $79-$98, NONSTOP. Flights October to March. Weekends available. Origin/Destination reversible.

Change fees are waived and carry-on bag is allowed for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Patreon supporters receive a recap of all the airfare deals currently available everyday.

We don’t charge a subscription fee. Our deal notifications are available for FREE via Instagram, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

Click for more details and booking links Nonstop Flights: Los Angeles to/from Chicago $79-$98 r/t [October-March] – American Airlines / Alaska Airlines

Airfare Deals Alaska Airlines American Airlines Bookable Chicago Bookable Deals Bookable LAX Chicago Flights from Chicago / Milwaukee Flights from Los Angeles Oneworld

United and American have round-trip flights from Chicago (ORD) to Paris or Barcelona (CDG/BCN) for $491-$513, NONSTOP. Flights March, April, May, and August. Extended weekends available.

Covid restrictions are still in place, but this may be worthwhile for the 2021 dates.

Change fees are being waived by American and Untied waived.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Patreon supporters receive a recap of all the airfare deals currently available everyday.

We don’t charge a subscription fee. Our deal notifications are available for FREE via Instagram, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

Click for more details and booking links Nonstop Flights: Chicago to Paris or Barcelona $491-$513 r/t [Mar, Apr, May, Aug 2021] – United / American

Airfare Deals Bookable Chicago Bookable Deals Flights from Chicago / Milwaukee Paris Star Alliance United

American Airlines and United has round-trip flights from Chicago (ORD) to Las Vegas (LAS) for $75, NONSTOP. Flights December to March. No Friday departures. Extended weekends available. Origin/Destination reversible.

Carry-on bag is allowed for free on AA. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Patreon supporters receive a recap of all the airfare deals currently available everyday.

We don’t charge a subscription fee. Our deal notifications are available for FREE via Instagram, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

Click for more details and booking links Nonstop Flights: Chicago to/from Las Vegas $75 r/t [December-March] – American Airlines / United

Airfare Deals American Airlines Bookable Chicago Bookable Deals Flights from Chicago / Milwaukee Las Vegas Oneworld

American Airlines has round-trip flights from Chicago (ORD) to San Diego, Austin, Seattle, or Orlando (SAN, AUS, SEA, MCO) for $71-$75, NONSTOP. Flights October to April. Weekends available. Origin/Destination reversible.

Change fees are waived and carry-on bag is allowed for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Patreon supporters receive a recap of all the airfare deals currently available everyday.

We don’t charge a subscription fee. Our deal notifications are available for FREE via Instagram, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

Click for more details and booking links Nonstop Flights: Chicago to/from San Diego, Austin, Seattle, or Orlando $71-$75 r/t [October-April] – American Airlines

Airfare Deals American Airlines Bookable Chicago Bookable Deals Flights from Chicago / Milwaukee Oneworld San Diego

American Airlines has round-trip flights from Chicago (ORD) to New Orleans, Dallas, Denver, or Atlanta (MSY, DFW, DEN, ATL) for $71-$107, NONSTOP. Flights October to April. Weekends available. Origin/Destination reversible. Holiday dates are available for New Orleans, Dallas, and Atlanta.

Change fees are waived and carry-on bag is allowed for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Patreon supporters receive a recap of all the airfare deals currently available everyday.

We don’t charge a subscription fee. Our deal notifications are available for FREE via Instagram, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

Click for more details and booking links Nonstop Flights: Chicago to/from New Orleans, Dallas, Denver, or Atlanta $71-$107 r/t [October-April + Christmas/NYE] – American Airlines

Airfare Deals American Airlines Bookable Chicago Bookable Deals Flights from Chicago / Milwaukee New Orleans Oneworld

American Airlines has round-trip flights from Chicago (ORD) to Portland (PDX) for $88-$101, NONSTOP. Flights November to December. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Extended weekends available. Origin/Destination reversible. No Holiday dates were found.

Change fees are waived and carry-on bag is allowed for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Patreon supporters receive a recap of all the airfare deals currently available everyday.

We don’t charge a subscription fee. Our deal notifications are available for FREE via Instagram, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

Click for more details and booking links Nonstop Flights: Chicago to/from Portland $88-$101 r/t [November-December] – American Airlines

Airfare Deals American Airlines Bookable Chicago Bookable Deals Flights from Chicago / Milwaukee Oneworld Portland

Airfare Deals Bookable Chicago Bookable Deals Bookable LAX Bookable NYC Bookable Seattle / Portland Flights from Chicago / Milwaukee Flights from Los Angeles Flights from Milwaukee Flights from New York Flights from Portland Flights from Seattle / Portland

United has round-trip flights from Chicago (ORD) to Tahiti (PPT) for $877 with a connection. Flights September to February. Departures on Tuesday, Thursday, and Saturday. Extended weekends available.

Pre-flight negative Covid test is required to avoid mandatory quarantine restrictions. Change fees are waived and a carry-on bag is allowed for free.

Want a notification sent straight to your phone when any new deals are found? Join our Telegram channel and never miss another deal.

Patreon supporters receive a recap of all the airfare deals currently available everyday.

We don’t charge a subscription fee. Our deal notifications are available for FREE via Instagram, Facebook, Twitter, Telegram, our Webpage, and our E-mail list. If you are paying someone a subscription fee for this content, you are being ripped off.

Click for more details and booking links Cheap Flights: Chicago to Tahiti $877 r/t [September-February] – United

Airfare Deals Bookable Chicago Bookable Deals Flights from Chicago / Milwaukee Star Alliance Tahiti United