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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.

Been thinking about a trip to Windy City? Now’s the perfect time to book. We’re currently seeing flights to Chicago (ORD) from numerous cities across the US, including Los Angeles (LAX), Seattle (SEA), Miami (MIA) and Boston (BOS) from as low as $48 one-way or just 3,220 points if you have a Chase Sapphire Reserve and book through the Chase Ultimate Rewards travel portal. The lowest fares are being offered by American, Alaska, Delta and United and are available for travel between September 2019 and February 2020.

Most of these fares book into basic economy, meaning added fees and more restrictions in return for the attractive price. Fortunately, all of the major carriers, except for United, still allow you to bring a carry on bag with a basic economy ticket. Keep in mind that you can combat some of the negative aspects of basic economy by using your airline elite status or a carrier’s co-branded credit card.

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To search for these fares, head to Google Flights and enter your origin and destination cities. Scroll through the calendar function to find dates and prices that work for you. Finally, click through to book directly with the airline, through an OTA like Priceline or plug those dates into the Ultimate Rewards travel portal.

Airlines: American, Alaska, Delta, United
Routes: BOS/LAX/LGA/JFK/MIA/FLL/PHX/LAS/DFW/IAH/SEA to/from ORD
Cost: $48+ or 3,220+ Ultimate Rewards points one-way in basic economy
Travel Dates: September 2019 to February 2020
Pay With: The Platinum Card® from American Express (5x on airfare booked directly with the airline), Citi Prestige Card (5x on airfare plus excellent trip delay insurance), Citi Premier CardChase Sapphire ReserveAmerican Express® Gold Card (3x on airfare when booked directly with the airline) or Chase Sapphire Preferred Card (2x on travel)

Here are a few examples of what you can book:

Dallas (DFW) to Chicago (ORD) for $48 or 3,220 points one-way in American basic economy:

Fort Lauderdale (FLL) to Chicago (ORD) for $54 or 3,620 points one-way in American basic economy:

Los Angeles (LAX) to Chicago (ORD) for $56 or 3,753points one-way in United basic economy:

Phoenix (PHX) to Chicago (ORD) for $63 or 4,220 points one-way in American basic economy:

Las Vegas (LAS) to Chicago (ORD) for $64 or 4,286 points one-way in American basic economy:

Boston (BOS) to Chicago (ORD) for $71 or 4,753 points one-way in Delta basic economy:

Seattle (SEA) to Chicago (ORD) for $81 or 5,420 points one-way in Alaska saver 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), Citi Prestige Card (5x on airfare on plus excellent trip delay insurance), Chase Sapphire ReserveAmerican Express® Gold CardCiti Premier Card (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 Kevin Young / Unsplash.

Know before you go.

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2018 TPG Award Winner: Mid-Tier Card of the Year
Chase Sapphire Preferred® Card

NEW INCREASED OFFER: 60,000 Points

TPG'S BONUS VALUATION*: $1,200

CARD HIGHLIGHTS: 2X points on all travel and dining, points transferrable to over a dozen travel partners

*Bonus value is an estimated value calculated by TPG and not the card issuer. View our latest valuations here.

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More Things to Know
  • Earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $750 toward travel when you redeem through Chase Ultimate Rewards®
  • 2X points on travel and dining at restaurants worldwide & 1 point per dollar spent on all other purchases.
  • Get 25% more value when you redeem for airfare, hotels, car rentals and cruises through Chase Ultimate Rewards. For example, 60,000 points are worth $750 toward travel
Intro APR on Purchases
N/A
Regular APR
18.24% - 25.24% Variable
Annual Fee
$95
Balance Transfer Fee
Either $5 or 5% of the amount of each transfer, whichever is greater.
Recommended Credit
Excellent/Good

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