Category: <span>Flights from Chicago / Milwaukee</span>

Frontier has round-trip flights from Chicago (ORD) to Denver (DEN) for $39-$47, NONSTOP. Flights January to March. Very few weekends available. Origin/Destination reversible.

Note: Frontier fares do not include a free carry-on bag. Only a small personal item, like a Jansport City Scout backpack is free. You can avoid paying for seat selection if you accept the randomly assigned seat prior to boarding.

Note: Frontier seats only have 28-inches of pitch; 2-to-3 inches less space than most other airlines.

Iā€™m currently using the Jansport Right Pack as my “personal item” when I fly Frontier. Which is slightly more than expensive than the Jansport City Scout because its fabric is Cordura instead of Polyester. Both have the same dimensions which are: 18″ x 13″ x 8.5″. There is half-an-inch of extra depth than what is officially allowed by Frontier, but it has never been a problem for me. The bag has a large main compartment, which makes it ideal for stuffing as much as you can into the limited amount of space.

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Click for more details and booking links Nonstop Flights: Chicago to/from Denver $39-$47 r/t [January-March] – Frontier

Airfare Deals Bookable Chicago Bookable Deals Denver Flights from Chicago / Milwaukee Frontier

American Airlines has round-trip flights from Chicago (ORD) to Nassau (NAS) for $361, NONSTOP. Flights February to August. Departures on Saturday. Origin/Destination reversible. 7-day minimum stay required.

A negative COVID PCR test result is required for entry.

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 Nassau, Bahamas $361 r/t [February-August] – American Airlines

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

American Airlines has round-trip flights from Chicago (ORD) to Saint Croix (STX) for $204-$207 with a connection. Flights January to June. Weekends available.

A negative COVID PCR test result is required for entry.

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 Saint Croix $204-$207 r/t [January-June] – American Airlines

Airfare Deals American Airlines Bookable Chicago Bookable Deals Flights from Chicago / Milwaukee Oneworld Saint Croix

JetBlue has round-trip flights from Chicago (ORD) to Nassau (NAS) for $305 with a connection. Flights February to March.

A negative COVID PCR test result is required for entry [details linked].

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 Nassau, Bahamas $305 r/t [February-March] – JetBlue

Airfare Deals Bookable Chicago Bookable Deals Flights from Chicago / Milwaukee JetBlue Nassau

United and American Airlines has round-trip flights from Chicago (ORD) to Denver (DEN) for $83-$95, NONSTOP. Flights January to May. Weekends available.

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: Chicago to Denver $83-$95 r/t [January-May] – American Airlines / United

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

American Airlines has round-trip flights from Chicago (ORD) to Reno or San Antonio (RNO/SAT) for $97, NONSTOP. Flights in March. No Weekends. Departures on Monday, Tuesday, Wednesday, and Thursday.

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 Reno or San Antonio $97 [March] r/t – American Airlines

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

American Airlines has round-trip flights from Los Angeles (LAX) to Chicago (ORD) for $83, NONSTOP. Flights January to May. Weekends available. Origin/Destination is 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 $83 r/t [January-May] – American Airlines

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 Miami or Tampa (MIA/TPA) for $83-$90, NONSTOP. Flights January to May. Mostly weekdays. 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 Miami or Tampa $83-$90 r/t [January-May] – American Airlines

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

American Airlines has round-trip flights from Chicago (ORD) to Fort Myers (RSW) for $83-$90, NONSTOP. Flights January to April. Departures on Monday, Tuesday, and Sunday. 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 Fort Myers $83-$90 r/t [January-April] (Mon/Tue/Sun) – American Airlines

Airfare Deals American Airlines Bookable Chicago Bookable Deals Flights from Chicago / Milwaukee Fort Myers Oneworld

United has round-trip flights from Chicago (ORD) to Punta Cana (PUJ) for $188-$200, NONSTOP. Flights January to March. Very few weekends available.

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.

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 Punta Cana, Dominican Republic $188-$200 r/t [January-March] – United

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