Round-trip fares to Chicago, including summer travel dates, starting at $150

May 16, 2022

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Chicago is among the country’s greatest cities to visit during the summer, which is why we are doing you a favor and alerting TPG readers about round-trip flights to Chicago, starting at $150, including peak summer availability.

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Deal basics

(Photo by Nagehan Demirci/EyeEm/Getty Images)

Airlines: United, JetBlue, American and Southwest
Routes: EWR/BOS/JFK/LGA/IAD/DCA/MIA and others to ORD
How to book: Directly through the airline
Travel dates: July 2022 — March 2023
Book by: 2—3 days

Props to Scott’s Cheap Flights for sending us this deal. Sign up for a Premium membership and get deals up to 90% off, which users can try for free for 14 days or $49 per year. You can also upgrade to the Elite tier for $199 per year and receive all the Premium deals plus premium economy, business-class and first-class alerts.

Sample routes

The good news is that this deal features flights for less than $200 departing from a wide variety of U.S. cities, including:

  • Boston (BOS) starting at $150
  • New Haven (HVN) starting at $158
  • Colorado Springs (COS) starting at $168
  • Minneapolis (MSP) starting at $178
  • Miami (MIA)/New York City (JKF/LGA)/Fayetteville (XNA)/Fort Lauderdale (FLL)/Sioux Falls (FSD) starting at $188
  • Baltimore (BWI)/Washington, D.C. (IAD/DCA) starting at $198

Additionally, you can find fights for slightly more than $200, including from Burlington (BTV) starting at $208, Denver (DEN) starting at $218 and Houston (HOU) starting at $227.

To search for this deal, head to Google Flights and enter your origin city and ORD as your destination. For example, this round-trip, nonstop EWR-ORD flight is just over $200. This flight is a good deal considering the normal price for this route is nearly $300.

However, this particular flight is for a fare on United’s basic economy class, which does not include full-sized carry-on luggage.

Read more: Sold-out summer: 31 travel tips to keep your trip on track and on budget

(Screenshot courtesy of Google Flights)

To get around this, consider upgrading to economy for $60, which would still be approximately $100 cheaper than the other flights available on this day for this route since the same flight on American Airlines starts at $352 for their main cabin.

(Screenshot courtesy of Google Flights)

If you have flexibility with your airports, consider departing from LGA and arriving at MDW to fly Southwest, which offers that route for the same dates for a sweet spot right in the middle of the United and AA fares, at $282.

All things considered, this may actually be the best flight option for New York City-based travelers since all SWA fares include two free checked bags, in addition to two carry-ons, specifically one that fits underneath the seat in front of you and a larger bag for the overhead bin.

(Screenshot courtesy of Southwest Airlines)

Since Google Flights omits Southwest flights in their search engine, I always recommend reviewing their low fare calendar ahead of booking. Flying Southwest over another domestic carrier is particularly useful when the cheapest fare listed omits baggage, which is the case for United’s basic economy and JetBlue’s Blue Basic and Blue fares.

Related: Memorial Day weekend start of busy summer travel season just 3 weeks away

(Screenshot courtesy of Southwest Airlines)

Maximize your purchase

Don’t forget to use a card that earns bonus points on airfare purchases, such as The Platinum Card® from American Express (5 points per dollar on airfare booked directly with the airline or through American Express Travel), on up to $500,000 on these purchases per calendar year, Citi Prestige® Card (5 points per dollar on airfare), Citi Premier® Card, Chase Sapphire Reserve (3 points per dollar on airfare), American Express® Gold Card (3 points per dollar on airfare when booked directly with the airline or through Amex Travel) or the Chase Sapphire Preferred Card (2 points per dollar on travel). Check out this post for more on maximizing airfare purchases.

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.

Bottom line

(Photo by Mlenny/Getty Images)

Although this deal includes flights for upcoming summer travel, as well as deals through December and into early 2023, this is a particularly good deal for last-minute summer trips since airfares for the summer have continued to increase.

Read more: New technology for TSA could reduce airport wait times this ‘sold-out summer’

Featured photo by Ken Ilio/Getty Images.

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