The 5 Best Credit Cards for a Chicago-Based Traveler

Jul 12, 2016

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There are plenty of great rewards-earning credit cards to choose from, but depending on where you live and which airlines best serve your hub airport, some of them are better choices than others. Below, TPG Senior Points & Miles Contributor Nick Ewen takes a look at the top options for travelers flying out of Chicago.

If you’re like me, you probably think very carefully about which travel rewards credit cards to open and carry in your wallet. Some offer limited-time sign-up bonuses, while others give you lucrative bonus categories for different types of purchases. Geography can also play a role in your decision-making process, and today I’ll continue my series that identifies the best cards for residents of certain cities. After starting with New York and then Atlanta, I’ll now move on to the Windy City.

If you’re based in Chicago, which card is best for earning free flights? Image courtesy of Shutterstock.

To answer the question of which cards are best for a Chicago-based traveler in today’s post (as well as future posts for other major cities), I’ll be following a straight-forward format that looks at the following characteristics of a given card:

  • Sign-up bonus
  • Earning rates
  • Other benefits
  • Annual fee

I’ll then detail out why that particular card would appeal to Chicagoans. Finally, I’ll note another one or two similar options any highlight the key difference(s) you’d notice.

Before getting into the analysis, a few disclaimers. For starters, this list is aimed mainly at leisure travelers who are interested in maximizing their rewards on credit cards. If you regularly travel for business and earn elite status, the calculus may change significantly, as you have additional ways to earn points and miles, and some of the benefits I tout below may be included. Fierce loyalty to a single airline may also lead you away from cards offered by a competitor, though I would strongly encourage you to diversify in the event of a mass-scale devaluation (like we recently saw with American).

In addition, this list represents just one way of looking at the situation and is geared mainly at free flights. You may simply want a card that offers solid everyday value for other rewards (like the Citi Double Cash Card for cash back or the Citi Hilton HHonors Reserve Card for free hotel stays). As always, feel free to adjust the list based on your own situations.

Now that we’ve gotten that out of the way, which cards are best for a Chicago-based award traveler? In no particular order:

1. Citi / AAdvantage Platinum Select World Elite Mastercard

Sign-up bonus: 60,000 miles after spending $3,000 in purchases within the first three months of account opening
Earning rates: 2 miles per dollar spent on American Airlines purchases, at gas stations and restaurants; 1 mile per dollar spent everywhere else
Other benefits: No foreign transaction fees; reduced mileage awards; first checked bag free; 25% off in-flight purchases
Annual fee: $99 (waived for the first year)

Analysis: One of American Airlines’ largest hubs is Chicago-O’Hare International Airport, with flights to more than 120 destinations around the world. There are also numerous partner airlines with service from O’Hare, including Cathay Pacific (to Hong Kong), British Airways (to London-Heathrow), Etihad (to Abu Dhabi) and Alaska Airlines (to Seattle and Anchorage). This gives you numerous options to redeem your miles all over the globe, though many premium-class redemptions were increased in March.

In addition, the AAdvantage Platinum Mastercard will help make your American travel experience a bit less stressful (and less costly). You and four companions on the same reservation can check a bag for free on all AA flights, saving up to $50 per person on a round-trip domestic flight. You’ll also enjoy preferred boarding, and 25% off in-flight purchases. Finally, if you head outside the US, the card doesn’t charge any foreign transaction fees.

The information for the Citi AAdvantage Platinum 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.   

Other option(s): Citi / AAdvantage Executive World Elite Mastercard (includes Admirals Club membership but carries a $450 annual fee)

2. United MileagePlus Explorer Card

united @ ord
United also utilizes O’Hare as a key hub, making the Explorer Card another terrific option.

Sign-up bonus: 30,000 bonus miles after you spend $1,000 on purchases in the first three months your account is open plus 5,000 bonus miles when you add the first authorized user and make a purchase in the first three months
Earning rates: 2 miles per dollar spent on United tickets; 1 mile per dollar spent on all other purchases
Other benefits: Free checked bag; priority boarding; 2 United Club passes each year; no foreign transaction fees; 10,000 bonus miles when you spend $25,000 each calendar year
Annual fee: $95 (waived for the first year)

Analysis: Another carrier that utilizes O’Hare as its hub is United, offering nonstop service to nearly 200 destinations around the globe. United also has many Star Alliance partners with service out of Chicago, including ANA (to Tokyo), Swiss (to Zurich) and Lufthansa (to Munich and Frankfurt). Just remember that United went through its own devaluation back in February 2014, so your miles won’t go nearly as far as they used to, especially on partner flights.

The card also provides Chicago-based travelers with a number of key benefits when traveling on United. You and one travel companion on the same reservation will enjoy a free checked bad on all United flights, though you must pay for the ticket with your card to utilize this perk. You’ll also enjoy priority boarding and a 20% in-flight discount, and if you’re also an elite member, the card will enable you to be upgraded on award tickets. However, one of the most valuable perks is the additional award inventory it opens up, which can save the day if your desired flight only has standard inventory or if you find partner award inventory and need a connecting United flight to make it work.

Other option(s): United MileagePlus Club Card (includes United Club access but carries a $450 annual fee)

3. Southwest Rapid Rewards Premier Credit Card

Southwest plane on ground Las Vegas 2 featured
Southwest can open up a wealth of redemption options from Chicago’s Midway Airport.

Sign-up bonus: 40,000 points after you spend $1,000 on purchases in the first three months
Earning rates: 2 points per dollar spent on Southwest purchases and Rapid Rewards hotel and car rental partner purchases; 1 point per dollar everywhere else
Other benefits: 6,000 points after your cardmember anniversary; no foreign transaction fees; 1,500 Tier Qualifying Points (TPQs) for every $10,000 spent in a year (up to 15,000 TQPs)
Annual fee: $99

Analysis: If you’d rather avoid the sprawling complex of O’Hare (or if you live in South Chicago or the southern suburbs), you may prefer traveling out of Chicago-Midway (MDW). If that’s the case, Southwest is a fantastic option. Midway is actually one of Southwest’s largest hubs, with nonstop service to more than 60 destinations. While you won’t be able to enjoy luxurious international flights on Southwest, the carrier does provide a decent in-flight experience and can keep cash in your pocket when traveling out of Chicago. The increased sign-up bonus on this card should get you around $750 worth of free flights, and the carrier’s no-fee change policy applies to award tickets as well.

The card also provides an anniversary bonus of 6,000 points, which covers most of the $99 annual fee, and you won’t pay foreign transaction fees when traveling abroad. In addition, you’ll earn 1,500 Tier Qualifying Points (TQPs) for every $10,000 you spend on the card (up to 15,000 TQPs per year). Finally, and possibly most importantly, the points you earn on the card (including the sign-up bonus) will count toward the Companion Pass each year. This is one of the most lucrative perks in the frequent flyer world, allowing you to bring a companion along on all paid and award flights. If you can earn this pass living in Chicago (and the Southwest Premier Card is a great way to start), you can get a ton of value out of it!

Other option(s)Southwest Rapid Rewards Plus Credit Card (same sign-up bonus and lower annual fee but lower anniversary bonus and a 3% foreign transaction fee)

4. British Airways Visa Signature Card

British Airways plane 777 Heathrow featured
British Airways not only offers regular service out of Chicago but also opens up many redemption options on short-haul American flights.

Sign-up bonus: Earn up to 100,000 bonus Avios. Earn 50,000 bonus Avios after spending $3,000 on purchases within the first three months of account opening. Plus, an additional 25,000 bonus Avios after spending $10,000 total within the first year and an extra 25,000 Avios after spending $20,000 total within the first year.
Earning rates: 3 Avios per dollar spent on British Airways purchases; 1 Avios per dollar everywhere else
Other benefits: No foreign transaction fees; Travel Together Ticket; 10% discount on British Airways flights
Annual fee: $95

Analysis: Another option to consider as a Chicago resident is the British Airways Visa. This is partly due to the multiple daily flights offered to London-Heathrow, but it also works wonders if you want to redeem your points for short-haul American flights. British Airways’ distance-based award chart allows you to redeem just 7,500 Avios for one-way flights of 1,151 miles or less. From Chicago O’Hare, this includes virtually all of the Eastern, Central and Mountain time zones:

Screen Shot 2016-05-31 at 3.57.01 PM

The card also provides other perks, though the earning rates were changed last year. You’ll enjoy 10% off paid British Airways flights using the code CARDOFFERU at, and if you spend $30,000 on the card in a calendar year, you’ll earn a Travel Together ticket that allows you to bring a companion along when you redeem your Avios for a British Airways flight departing from the US (though you will need to pay taxes and fees, which can be quite high for premium-class redemptions). Like the others above, the card also doesn’t incur foreign transaction fees.

Other option(s): N/A

5. Chase Sapphire Preferred Card

Sign-up bonus: Earn 50,000 bonus points after you spend $4,000 on purchases in the first three months from account opening. That’s $625 in travel when you redeem through Chase Ultimate Rewards.
Earning rates: 2x points on travel and dining at restaurants and 1 point per dollar spent on all other purchases worldwide
Other benefits: $0 in foreign transaction fees; primary car rental insurance
Annual fee: $0 for the first year, then $95

Analysis: If you don’t want to commit to a single airline, another terrific card for Chicago-based flyers is the Chase Sapphire Preferred. The Ultimate Rewards points you’ll earn are among the most valuable out there, and you can transfer points to United, Southwest and British Airways, giving you the flexibility to choose which carrier you want to fly when you’re ready to book. This also doesn’t even factor in the hotel transfer options like Marriott and (my personal favorite) Hyatt. While Ultimate Rewards points can also be redeemed directly for travel at a rate of 1.25 cents apiece, you’ll generally get much better value when transferring them to partner programs.

The Sapphire Preferred card also offers some great value on spending, with 2x points on dining and virtually all travel purchases. These categories are quite expansive, including merchants like Uber, toll agencies and bars that don’t even serve food. You’ll also pay no foreign transaction fees and enjoy primary car rental insurance. Both TPG and I use this card for a majority of our purchases, and we’ve both gotten some fantastic value out of the Ultimate Rewards program.

Other option(s): Ink Plus Business Card (higher sign-up bonus and 5x bonus categories but 2x category only applies to gas stations and hotel accommodations)

Bottom Line

There are many factors to consider when applying for a new credit card, and if you want to redeem your points or miles for free flights, geography can play a key role. As always, be sure to evaluate your own spending habits and desired redemptions, but hopefully this post has given you some guidance for choosing the best credit card option(s) if you currently live in Chicago.

For the Chicago-based TPG readers out there, what’s your favorite credit card for award travel?

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.