Category: <span>Bookable Chicago</span>

Delta has round-trip flights from Chicago (ORD) to San Juan (SJU) for $116 with a connection. Flights December to February. Weekends available. Origin/Destination reversible.

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

Change fees are being 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.

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Click for more details and booking links Cheap Flights: Chicago to/from San Juan, Puerto Rico $116 r/t [December-February] – Delta

Airfare Deals Bookable Chicago Bookable Deals Delta Flights from Chicago / Milwaukee San Juan SkyTeam

United and American Airlines have round-trip flights from Chicago (ORD) to San Francisco (SFO) for $137, NONSTOP. Flights January to May. Departures on Tuesday, Wednesday, and Saturday. Extended 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.

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Click for more details and booking links Nonstop Flights: Chicago to/from San Francisco $137 r/t [January-May.2021] – American Airlines / United

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

United has round-trip flights from Chicago (ORD) to Punta Cana (PUJ) for $182, NONSTOP. Flights December to May. Weekends available. Origin/Destination reversible.

A negative COVID PCR test result may be required for entry.

Change fees are waived, but United’s “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.

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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Click for more details and booking links Nonstop Flights: Chicago to/from Punta Cana, Dominican Republic $182 r/t [December-May.2021] – United

Airfare Deals Bookable Chicago Bookable Deals Flights from Chicago / Milwaukee Punta Cana Star Alliance United

United has round-trip flights from Chicago (ORD) to Cancun (CUN) for $136, NONSTOP. Flights December to May. Weekends available. Origin/Destination reversible.

Change fees are waived and fares include a free carry-on bag.

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Click for more details and booking links Nonstop Flights: Chicago to/from Cancun $136 r/t [December-May 2021] – United

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

[11/12/2020 @ 12:47 PM CT] Fare was removed by Delta. If it goes back online, we will send out another notification.

Delta has round-trip flights from Chicago (ORD) to Lima (LIM) for $296 with a connection. Flights in January, April, May, August, and September. No Weekends. Departures on Monday, Tuesday, Wednesday, and Thursday.

Change fees are being 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.

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Click for more details and booking links Cheap Flights: Chicago to Lima $296 r/t – Delta

Airfare Deals Bookable Chicago Bookable Deals Delta Flights from Chicago / Milwaukee Lima SkyTeam

American Airlines and United have round-trip flights from Los Angeles (LAX) to Chicago (ORD) for $75, NONSTOP. Flights November to March. No Sunday departures. A few weekends available. Origin/Destination reversible.

Change fees are waived and carry-on bag is allowed for free on American. United charges an additional fee for carry-on bags. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

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

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

American Airlines has round-trip flights from Chicago (ORD) to Cancun (CUN) for $166-$173, NONSTOP. Flights November to March. No Thursday departures. Very few 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.

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Click for more details and booking links Nonstop Flights: Chicago to/from Cancun $166-$173 r/t [November-March] – American Airlines

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

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.

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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.

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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.

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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