Category: Bookable Chicago

United has round-trip flights from Chicago (ORD) to Cancun (CUN) for $164, NONSTOP. Flights October to February. No Weekends. Departures on Monday, Tuesday, Wednesday, and Thursday. Extended Weekends available. Origin/Destination reversible.

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/from Cancun $164 r/t [October-February.2021] – United

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

[07/10/2020 @ 04:48 PM CT] Deal is back on.

United, Delta and American Airlines have round-trip flights from Chicago (ORD) to Cleveland, Columbus, Cincinnati, Detroit, Indianapolis, Memphis, or Nashville (CLE, CMH, CIN, DTW, IND, MEM, BNA) for $97, NONSTOP. Flights July to December. Departures on Monday, Tuesday, Wednesday, Thursday, and Saturday. Extended Weekends available. Origin/Destination reversible.

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 Cleveland, Columbus, Cincinnati, Detroit, Indianapolis, Memphis, or Nashville $97 r/t – United / American Airlines / Delta

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

United and American Airlines have round-trip flights from Chicago (ORD) to Philadelphia (PHL) for $75-$76, NONSTOP. Flights July to February. Weekends available. Origin/Destination reversible.

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

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Click for more details and booking links Nonstop Flights: Chicago to/from Philadelphia $75 r/t [July-February.2021] – United / American Airlines

Airfare Deals American Airlines Bookable Chicago Bookable Deals Flights from Chicago / Milwaukee Oneworld Philadelphia Star Alliance United

JetBlue has round-trip flights from Chicago (ORD) to Aruba (AUA) for $220-$235 with a connection. Flights September to October. Very few weekends available. Origin/Destination reversible.

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

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Click for more details and booking links Cheap Flights: Chicago to/from Aruba $220-$235 r/t [September-October] – JetBlue

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

United has round-trip flights from Chicago (ORD) to Vancouver (YVR) for $199-$216, NONSTOP. Flights September to May. Weekends available. Origin/Destination reversible.

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Click for more details and booking links Nonstop Flights: Chicago to/from Vancouver $199-$216 r/t [September-May.2021] – United

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

American Airlines has round-trip flights from Chicago (ORD) to Denver (DEN) for $49, NONSTOP. Flights August to February. 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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Patreon supporters receive a recap of all the airfare deals currently available everyday.

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Click for more details and booking links Nonstop Flights: Chicago to/from Denver $49 r/t [August-February] – American Airlines

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

American Airlines has round-trip flights from Newark/New York (EWR) to Chicago (ORD) for $65-$73, NONSTOP. Flights July to November. 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.

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Click for more details and booking links Nonstop Flights: Newark/New York to/from Chicago $65-$73 r/t [July-November] – American Airlines

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

Delta and Alaska Airlines have round-trip flights from Milwaukee (MKE) to Anchorage (ANC) for $288 with a connection. Flights August to September. No Sunday departures. Weekends available. Origin/Destination reversible.

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.

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: Milwaukee to/from Anchorage $288 r/t [August-September] – Delta / Alaska Airlines

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

United has round-trip flights from Milwaukee (MKE) to Aspen (ASE) for $186-$210 with a connection. Flights August to November. Extended 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. 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).

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: Milwaukee to Aspen $186-$210 r/t [August-November] – United

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

COPA has round-trip flights from Chicago (ORD) to San Jose, Costa Rica (SJO) for $206 with a connection. Flights November to May. Weekends available.

Note: Some small OTAs on Skyscanner have this for $173. If you plan on booking there, beware of any site that charges a fee to cancel a ticket within the 24-hour “free” period. Use unknown booking sites at your own risk.

You can save up to an additional $150 on Flight+Hotel packages on Travelocity by using the “WANDER150” coupon-code at checkout.

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 San Jose, Costa Rica $173-$206 r/t [November-May.2021] – COPA

Airfare Deals Bookable Chicago Bookable Deals Copa Costa Rica Flights from Chicago / Milwaukee San Jose