The Best Travel Rewards Credit Cards for Chicago-Based Flyers

Like many of the world’s busiest cities, Chicago is served by multiple airports — namely, Chicago O’Hare (ORD) and Chicago Midway (MDW).

In terms of passenger traffic, O’Hare is the second-largest airport in the U.S. (8th in the world). Serving over 270 destinations, O’Hare is Chicago’s international gateway. While Midway Airport is significantly smaller, it’s still mighty, serving nearly 100 destinations. Midway is primarily a domestic airport, though it offers a handful of international options to Mexico and the Caribbean.

Its most popular destinations include New York (LGA), Los Angeles (LAX), Denver (DEN), London (LHR), and Cancun (CUN). But no matter where you’re flying, you can likely get there with a nonstop flight from one of Chicago’s airports.

Here’s what you need to know to optimize your Chicago-based credit card strategy.

What should Chicago travelers consider for their credit card strategy

Chicago O’Hare is dominated by two legacy carriers: United Airlines and American Airlines. United is the dominant airline, capturing more than 39% of traffic, while American manages over 22%. Meanwhile, Chicago Midway is a Southwest hub, responsible for shuttling a whopping 92% of all passengers.

With this in mind, the airline credit card you should consider depends on both your preferred airline and the airport you most frequently use. You’ll likely want to hold a credit card co-branded by either United, American, or Southwest.

Top credit cards for Chicago-based travelers who prefer United

United℠ Explorer Card

The United℠ Explorer Card is a great mid-range airline credit card with all the necessities. From free checked bags to preferred boarding to decent travel insurance, the card is a jack-of-all-trades. Its notable features include discounted award seats (even on business class) and two free United Club lounge passes each year.

The United Explorer Card annual fee is waived the first year, so you can test out its perks before making any investment.

United Club℠ Card

The United Club℠ Card is United’s most impressive personal credit card. Think of it as a souped-up version of the United Explorer Card, with complimentary United Club membership, up to two free checked bags per person, hundreds of dollars in annual statement credits, and up to 20,000 United miles in award flight discounts each year. For those with status, the points add up fast, too. Elite status holders earn 7-11x points for every dollar spent on United flights, depending on tier. 

Chase Sapphire Reserve®

While not strictly a United Airlines credit card, the Chase Sapphire Reserve offers a handful of benefits similar to the United cards — and a handful of benefits you won’t. The card offers hundreds of dollars in annual statement credits, excellent travel insurance, and a flexible rewards currency that can be instantly converted into United miles (among other airline currencies) at a 1:1 ratio.

You’ll also get access to more than 1,800 airport lounges worldwide, including Chase Sapphire and Priority Pass lounges.

Chase Sapphire Preferred® Card

The Chase Sapphire Preferred is a mid-range version of the Chase Sapphire Reserve. The card includes an annual hotel credit for prepaid accommodation booked through Chase Travel℠, solid travel insurance, and rewards that can be instantly transferred to United at a 1:1 ratio.

This card is ideal for those who want to quickly rack up United miles, as its bonus categories are arguably more practical than what you’ll get with most United credit cards.

Top credit cards for Chicago-based travelers who prefer American Airlines

Citi® / AAdvantage® Executive World Elite Mastercard®

American Airlines’ top-of-the-line credit card is the Citi® / AAdvantage® Executive World Elite Mastercard®. It provides several hundred dollars in annual statement credits, and it confers elite-like benefits to those who don’t have AA status.

The Citi AAdvantage Executive’s best feature is its complimentary American Airlines Admirals Club membership. This allows you to enter over 50 Admirals Club locations (and more than 50 partner lounges) around the world. Admirals Club membership regularly costs up to $850, so paying the card’s $595 annual fee is a great way to get membership at a steep discount.

Citi Strata Elite℠

The Citi Strata Elite℠ is another premium travel credit card that offers access to more than 1,800 airport lounges worldwide and hundreds of dollars in annual statement credits. The card is handy for American Airlines flyers because its rewards currency, Citi ThankYou points, transfers instantly to American AAdvantage at a 1:1 ratio. 

And for times when you aren’t flying on American Airlines or its partners, you can also transfer your rewards to JetBlue TrueBlue, Virgin Atlantic Flying Club, Emirates Skywards, and many others.

Citi Strata Premier℠ Card

The Citi Strata Premier℠ Card is a less premium version of the Citi Strata Elite, but it’s superior in some aspects.

While you won’t get airport lounge access or the same impressive number of statement credits, you’ll still get an annual $100 credit when spending $500+ on a single prepaid hotel stay booked through Citi Travel (excluding taxes and fees). 

You’ll also earn the same flexible Citi ThankYou points. In fact, the Citi Strata Premier offers some of the most generous and useful bonus spending categories of any rewards credit card. For example, you’ll earn 3 points per dollar for common expenses like restaurants, groceries, gas stations, and air travel.

Top credit cards for Chicago-based travelers who prefer Southwest

Southwest credit cards

If Chicago Midway is your preference, go all-in on Southwest credit cards.

Frequent travelers on Southwest are better off with the more premium cobranded cards, such as

• Southwest Rapid Rewards® Priority Credit Card

• Southwest® Rapid Rewards® Performance Business Credit Card

These cards give you Extra Legroom Seats when available and the ability to select a Standard seat at checkout (an important benefit for Southwest’s impending assigned seating). They also include a first checked bag free, preferred boarding, and much more.

Occasional Southwest fliers, on the other hand, will likely benefit more from low- to mid-tier cards, such as:

• Southwest Rapid Rewards® Plus Credit Card

• Southwest Rapid Rewards® Premier Credit Card

• Southwest® Rapid Rewards® Premier Business Credit Card

These cards still include one free checked bag and complimentary seat selection within 48 hours of travel.

Chase Sapphire Reserve®

Again, the Chase Sapphire Reserve® isn’t an airline-specific credit card — though it’s often a no-brainer for frequent flyers. Its annual travel credits can be redeemed for Southwest flights, and its points can be transferred instantly to Southwest at a 1:1 ratio.

And even though Southwest doesn’t have its own airport lounge network, the Chase Sapphire Reserve still gives you free entry into more than 1,800 Priority Pass airport lounges around the world.

Chase Sapphire Preferred® Card

The Chase Sapphire Preferred® Card is better for budget-conscious Southwest flyers. Though it doesn’t deliver the same recurring value, its annual fee is considerably lower. You’ll still get excellent benefits for the money, and your Chase points transfer to Southwest at a 1:1 ratio.

It’s also worth noting that both the Chase Sapphire Preferred and Chase Sapphire Reserve are ideal for those with no airline preference who want the freedom to fly out of both Chicago O’Hare and Chicago Midway. Nearly all of Chase’s airline transfer partners fly into Chicago, so you’ll have plenty of options, depending on where you’re going.

Why United, Southwest, and American Airlines cards are recommended for Chicago travelers

United, Southwest, and American Airlines credit cards are recommended for Chicago travelers because their benefits focus on the most popular airlines that serve Chicago’s two airports. You can receive free checked bags, award discounts, airport lounge access, preferred boarding, and much more with the airlines you fly the most.

Alternative airlines and credit cards from Chicago

If, as a Chicago-based traveler, you somehow manage to avoid the above airlines, you may be interested in a Delta credit card. Delta serves both O’Hare and Midway (albeit sparingly). Those who routinely fly from Chicago to Delta hubs like Atlanta (ATL), Minneapolis (MSP), or Detroit (DTW) may do better with the Delta SkyMiles® Gold American Express Card. It offers the first checked bag free, preferred boarding, discounts on Delta award flights (booked on Delta metal), and more.

The best cards for airport lounge access in Chicago

Chicago houses plenty of airport lounges, leaving you with a paralyzing selection. Here are some of the most popular credit card options for lounge access in Chicago.

United Club

United operates more than 45 Club airport lounges worldwide. Five of them are at Chicago O’Hare. You’ll find three in Terminal 1 (Concourse B, one near Gate B6 and one near Gate B18; Concourse C, near Gate C10) and two in Terminal 2 (Concourse E, near Gate E7; Concourse F, near Gate F9). You can enter these lounges with the following cards:

• United Club℠ Card

• United℠ Explorer Card (2 passes per cardmember year)

Admirals Club

American Airlines operates three Admirals Club lounges at Chicago O’Hare, all of which are in Terminal 3 (Concourse G near Gate G8, Concourse H/K between Gate H6 and Gate K6, Concourse L before Gate L1). You can enter these lounges with:

• Citi / AAdvantage Executive World Elite Mastercard

• Citi Strata Elite: (4 Admirals Club day passes per year, each valid for a 24-hour period to be used at multiple locations)

Delta SkyClub

Delta offers one lounge at Chicago O’Hare, located in Terminal 5 Concourse M, between Gates M14 and M11. You can enter this lounge with the following cards with an eligible same-day Delta fare:

• The Platinum Card® from American Express (10 visits per Medallion year; unlimited visits when spending $75,000 on the card in a calendar year)

• Delta SkyMiles® Reserve American Express Card (15 visits per Medallion year; unlimited visits when spending $75,000 on the card in a calendar year)

Air France Lounge

The O’Hare Air France Lounge is located in Terminal 5 (near Gate M17). Priority Pass lounge membership grants you access to this lounge, meaning those with the following cards have unlimited access:

• Chase Sapphire Reserve

• Citi Strata Elite

Swissport Lounge

Another popular Priority Pass-eligible lounge is the Swissport Lounge, also located in Terminal 5 (near Gate M13). You can enter this lounge with the Priority Pass Select membership you receive from cards like:

• Chase Sapphire Reserve

• Citi Strata Elite

Frequently asked questions

Are airline credit cards worth it if I only fly 2-3 times per year?

Airline credit cards are worth it even if you only fly two or three times per year. From statement credits to airline discounts to free checked bags, you may negate an airline credit card’s annual fee after a single trip.

How do I know which airline card to get if I fly from Chicago?

Chicago is dominated by three airlines: United, American, and Southwest. To choose the right airline card for your lifestyle, determine which of these airlines best suits your travel goals.

Should I get both American and United cards?

If you regularly fly on both American Airlines and United Airlines, it could be worth opening more than one airline credit card to ensure you get money-saving perks with both carriers.

What's the best strategy for earning United miles in Chicago?

The best strategy for earning United Airlines miles in Chicago is to use a United Airlines-earning credit card. If your primary goal is to earn United Airlines miles, we often recommend opening a card like the Chase Sapphire Preferred instead of a co-branded United credit card, as its bonus categories tend to be more generous. Chase points instantly transfer to United Airlines at a 1:1 ratio.

What's the best strategy for earning AA miles in Chicago?

The best strategy for earning AAdvantage miles in Chicago is to charge your purchases to a credit card that earns American miles. Instead of using an AAdvantage credit card for daily spending, consider a card like the Citi Strata Premier, which earns points that transfer to American Airlines at a 1:1 ratio. Its practical bonus categories blow AA credit card earning rates out of the water in most cases.