Deal alert: Round-trip flights to Chicago as low as $89

Oct 18, 2021

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The excitement I feel in bringing TPG a deal alert to Chicago, one of my most favorite cities, is unmatched. Scott’s Cheap Flights’ Elite membership alerted us to $100 round-trip economy fares to the Windy City, including some as low as $89.

With flights in the $100 range departing from across the U.S. — including Denver, Kansas City, Tampa and San Francisco — to Chicago’s O’Hare International Airport (ORD), run, don’t walk, to check out these fares now.

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(Photo by Bjarte Rettedal via Getty Images)

Airline: Alaska Airlines, American, Delta, JetBlue, United and Southwest.
Routes: ATL/DEN/DFW/FLL/MIA and others to ORD (and MDW for SWA flights).
Cost: As low as $89 round-trip for select routes.
Dates: Varies by route, but deals can be found for travel November-May, excluding Thanksgiving and Christmas.
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The information for the Citi Prestige Card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

As I mentioned, this deal is wide-reaching with most fares around $100-$200, flying from more than 100 U.S. cities. You can find outlier deals ranging in price from as low as $89 (Peoria, Illinois/PIA) to $236 (Bozeman Yellowstone International Airport/BZN) and the usual fares for Hawaii residents in the $300s.

Some of the best fares to ORD included in this package are out of:

  • Peoria (PIA) for $89 round-trip.
  • Miami (MIA) for $97 round-trip.
  • Minneapolis (MSP), Orlando (MCO), Phoenix (PHX) and Tampa (TPA) for $98 round-trip.
  • Indianapolis (IND) for $107 round-trip.
  • Austin, Texas (AUS), for $118 round-trip.
  • Buffalo, New York (BUF); Cleveland (CLE); New Orleans (MSY); and Syracuse, New York (SYR), for $127 round-trip.
  • Los Angles (LAX) for $133 round-trip.
  • Nashville (BNA) for $134 round-trip.
  • New York City (JFK) for $137 round-trip.
  • Washington, D.C. (DCA/IAD), for $147 round-trip.
  • San Fransisco (SFO) for $157 round-trip.
  • Providence (PVD) for $167 round-trip.
  • Seattle (SEA) for $177 round-trip.

To search for flights within this deal, head to Google Flights and enter your departure city of choice and Chicago (ORD) in the “Where to?” box. Let’s start with this nonstop JetBlue flight out of JFK to ORD in early November for $137 round-trip.

(Screenshot courtesy of Google Flights)

Although it matches the $137 price advertised in the deal, this flight would actually end up costing an additional $60 to carry on a bag because JetBlue’s Blue Basic fare does not include carry-on luggage. Alternatively, you could pay $50 more to upgrade to their Blue fare which includes one free carry-on for a fare totaling $187.

(Screenshot provided by Google Flights)

You could also evade JetBlue’s baggage fees by paying a bit more to fly American to Chicago on Nov. 9 and JetBlue on the way back on Nov. 14, such as the below flight.

(Screenshot courtesy of Google Flights)

Note that this flight would be a JetBlue-marketed ticket, meaning you would book through JetBlue versus American, thanks to the two airlines’ partnership offering a wider flight network with reciprocal loyalty benefits for members of both AAdvantage and TrueBlue.

Related: 11 must-do activities when visiting Chicago

Another extremely low fare in this deal is flying the almost 1,500 miles from Phoenix to Chicago on Nov. 1 and returning on Nov. 6, including this flight for less than $100 on United.

(Screenshot courtesy of Google Flights)

Once again, this route is for United’s basic economy fare, meaning it does not include a carry-on bag and a checked bag will run you $70. Upgrade to economy for $167 total and get that free carry-on.

(Screenshot courtesy of Google Flights)

To avoid baggage fees altogether, let’s look at Southwest Airlines, which is the only U.S. carrier that continues to allow flyers two free carry-on bags, specifically one that fits below the seat, like a backpack or purse, and a larger one better suited for the overhead bins. If you plan on checking luggage, your first two are also free, so a slightly more expensive SWA fare might end up saving you more money in bag fees charged by other carriers. Because Southwest Airlines flights do not show up in Google Flights, note that you will have to look up SWA flights manually on Chicago’s other airport, Midway (MDW), is a hub for SWA so you’ll likely find similarly priced flights as the ones included in the deal on other carriers.

For example, you could fly SWA from Miami (MIA) to MDW on Nov. 15 and return on Nov. 21 for just $49 each way, with flight selections outlined below.

(Screenshot courtesy of Southwest Airlines)
(Screenshot courtesy of Southwest Airlines)

The above flight would cost you $97.97, including taxes and fees.

(Screenshot courtesy of Southwest Airlines)

Before booking a trip to Chicago, note that a citywide indoor mask mandate remains in place since Aug. 20. Once you are in Chicago, there are plenty of things to do, but my favorites include walking or biking along Lake Michigan’s Lakefront Trail and Lincoln Park, stopping by the Bloomingdale’s (and other shops) on Michigan Avenue, taking an architecture boat tour and strolling along the Chicago Riverwalk.

(Photo by Andrey Denisyuk via Getty Images)

Read more: Unvaccinated? Think twice before booking trips to these 5 US cities

Featured photo by Reinier Snijders/EyeEm via Getty Images.

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