Deal Alert: Flights to Chicago From $88 Round-Trip in Basic Economy

Jul 26, 2018

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Airfare deals are typically only available on limited dates. We recommend you use Google Flights to find dates to fly, then book through an online travel agency such as Orbitz or Expedia, which allows you to cancel flights without penalty by 11pm Eastern Time within one day of booking. However, if you’re using The Platinum Card® from American Express, you’ll need to book directly with the airline or through the Amex Travel portal to get 5x MR points. Remember: Fares may disappear quickly, so book right away and take advantage of Orbitz or Expedia’s courtesy cancellation if you’re unable to get the time away from work or family.

Now’s a great time to book a trip to Chicago (ORD). American and United are currently offering flights to the Windy City — and vice versa — from major cities like Boston (BOS), Dallas (DFW) and New York (LGA) from $88 round-trip nonstop. Although the discounted fares are for basic economy, AA announced today that basic economy passengers will be allowed to travel with a carry-on bag (in addition to a personal item) starting September 5, so you might want to consider AA over United.

To find these low fares, head to Google Flights and plug in your desired departure and destination cities. After finding the dates that work best for you, book directly with the airline or with an OTA such as Expedia or Priceline. Google Flights has a feature which allows you to filter out no-carry-on bag fares, but it has not been updated yet to reflect AA’s changes. As a reminder, it’s possible to defeat many of basic economy’s negative aspects by having airline elite status or a co-branded airline credit card.

Airlines: American, United
Routes: BOS/DFW/IAH/JFK/LAS/LAX/LGA/MIA/PHX to/from ORD
Cost: $88+ round-trip in economy
Dates: August – December 2018
Booking Link: OrbitzExpedia or directly with the airline
Pay With: The Platinum Card® from American Express (5x on airfare), Chase Sapphire Reserve, Premier Rewards Gold Card from American Express, Citi Prestige (3x on airfare plus excellent trip delay insurance) or Chase Sapphire Preferred (2x on travel)

Here are a few examples of what you can book:

Boston (BOS) to Chicago (ORD) in September for $88 round-trip on United in basic economy:

Dallas (DFW) to Chicago (ORD) in August for $88 round-trip on United in basic economy:

Houston (IAH) to Chicago (ORD) in September for $88 round-trip on United in basic economy:

New York (LGA) to Chicago (ORD) in December for $137 round-trip on American in basic economy:

Las Vegas (LAS) to Chicago (ORD) in December for $138 round-trip on United in basic economy:

Miami (MIA) to Chicago (ORD) in September for $148 round-trip on American in basic economy:

Maximize Your Purchase

Don’t forget to use a credit card that earns additional points on airfare purchases, such as The Platinum Card® from American Express (5x on flights booked directly with airlines or American Express Travel), Chase Sapphire Reserve, American Express Premier Rewards Gold or Citi Prestige (3x on airfare) or the Chase Sapphire Preferred Card (2x on all travel purchases). Check out this post for more on maximizing airfare purchases.

Featured image by Sawyer Bengtson on Unsplash.

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