How to Book Award Flights from LAX to Chicago on 5 Major Airlines

While airline credit cards make it easy to rack up rewards with one airline, general travel cards may be the better choice.
Last updated June 2, 2023 | By Ben Luthi
Female tourist smiling in Chicago

We may receive compensation from the products and services mentioned in this story, but the opinions are the author's own. Compensation may impact where offers appear. We have not included all available products or offers. Learn more about how we make money and our editorial policies.

If you’re planning a trip from Los Angeles to Chicago, you’ll have plenty of airlines to choose from. And if you have frequent-flyer miles with a particular airline or credit card rewards with certain general travel programs, you may even be able to fly for free.

To help you score a flight from LAX (Los Angeles International Airport) to Chicago for the least amount of points or miles possible, here are some strategies to consider.

How to book award flights from LAX to Chicago on 5 popular airlines

If you have rewards with just one airline, your options will be limited. But if you have one of the best travel credit cards that allows you to transfer your points or miles to multiple airlines, you may have the choice between two or more, giving you greater flexibility.

Here’s how to book a flight from LAX to Chicago-area airports with six of the top airlines in the U.S.

1. Alaska Airlines

Alaska Airlines Mileage Plan miles can be incredibly valuable, with an average value of 1.8 cents apiece. While no general travel rewards programs allow you to transfer points to Alaska Airlines, you can transfer Marriott Bonvoy points at a 3:1 ratio. You can also earn miles with the Alaska Airlines Visa® Credit Card from Bank of America.

How many miles you need for a flight varies based on the date, fare class, and other factors. But we found both nonstop and connecting flights starting at 10,000 miles one way. If you prefer to fly first class, it will cost you 60,000 miles each way (or 25,000 each way with a mixed-cabin itinerary).

Note that some flights are operated by American Airlines through a code-sharing agreement. You can, however, still use your Mileage Plan miles to book those flights.

To book an Alaska Airlines flight with miles, visit the airline’s website and enter your itinerary, then choose “Miles only” as the award type. Should you not have enough miles to cover the round-trip fare, you can also choose “Miles & money” instead.

If you have some flexibility with your dates, the airline allows you to shop fares based on a monthly calendar. This will give you a better chance to score a flight with the least number of miles.

2. American Airlines

Like Alaska Airlines, American Airlines doesn’t have any general rewards program partners. But you can transfer Marriott Bonvoy points at a 3:1 ratio, and you can rack up rewards with several American Airlines credit cards, including:

When you’re ready to book a flight with American Airlines AAdvantage miles, you’ll have several fare options.

For starters, you’ll be able to choose between MileSAAver and AAnytime awards. The former requires fewer miles, but you’ll be limited on flight and seat options, making it a better option if you have a little flexibility. AAnytime awards allow you to book any seat — which is beneficial if your plans are set in stone — but they’re more expensive.

Along with these two choices, you’ll be able to pick a fare in economy, business/first, or first class. Here are the minimum amounts you can redeem for a free flight with each one:

  • Economy MileSAAver: 12,500 miles one way
  • Economy AAnytime: 20,000 miles one way
  • Business/First MileSAAver: 25,000 miles one way
  • Business/First AAnytime: 45,000 miles one way
  • First Anytime: 85,000 miles one way

Also, if you have an American Airlines credit card, you may be able to save up to 7,500 miles on round-trip MileSAAver fares. How much you’ll save with these reduced mileage awards can vary based on the card and the distance of your flight.

Remember that MileSAAver fares are restrictive, though, so you may have a hard time finding a nonstop flight. With an AAnytime award, both nonstop and connecting flights are available.

To book a flight, visit American Airlines’ website and enter your itinerary. Then check the box that states “Redeem miles.” From there, you can compare flights by fare class and award type to find the best option.

3. Delta Air Lines

Delta Air Lines partners with American Express Membership Rewards and Marriott Bonvoy, which allow you to transfer points at a 1:1 and 3:1 ratio, respectively. You can also earn Delta SkyMiles with any Delta credit card, including:

You’ll have four fare options when booking your flight. Here’s the minimum you can expect to pay with each (note that these are for round-trip tickets instead of one way):

  • Basic economy: 15,000 miles round trip
  • Economy: 21,000 miles round trip
  • Delta Comfort+: 33,000 miles round trip
  • First class: 55,000 miles round trip

If you don’t have enough miles, you can choose to book with a mix of miles and cash. One thing to keep in mind is that Delta doesn’t offer any nonstop flights from LAX to Chicago. So while booking with fewer miles than some of the other airlines we’ve listed is possible, it’s best if you don’t require a straight shot.

To book an award flight with Delta, visit the airline’s website and enter your itinerary. Then check the box for “Shop with Miles.” If your dates are flexible, you can compare rates with a fare calendar.

4. Southwest Airlines

You can transfer both Chase Ultimate Rewards points (1:1 ratio) and Marriott Bonvoy points (3:1 ratio) to the Southwest Rapid Rewards program. You can also earn rewards by using one of the airline’s co-branded credit cards:

Southwest Airlines doesn’t technically have different fare classes — it’s a first-come, first-serve boarding system. But there are three ticket types from which you can choose, and flight costs can vary with each one.

For example, Wanna Get Away fares are the cheapest but offer limited seating. Anytime fares don’t have award restrictions and allow you to do standby travel on a different flight to the same destination on the same date of travel, but they’re a bit pricier. Business Select is the most expensive fare type, but you’ll get priority boarding and a premium inflight drink.

Based on our research, we found the following point requirements for each option:

  • Wanna Get Away: 5,588 points one way
  • Anytime: 38,869 points one way
  • Business Select: 40,900 points one way

As you can see, it likely wouldn’t make sense to book anything but a Wanna Get Away fare. If you want priority boarding, you could save your points and upgrade at the airport for $30 to $50 per flight, depending on your itinerary.

To book a flight with Southwest, visit the airline’s website and enter your itinerary, then select the points option instead of dollars. If you have some flexibility with dates, you can compare flights with a fare calendar instead. Southwest offers both nonstop and connecting flights.

5. United Airlines

If you’re looking at United flights, you can transfer points from Chase Ultimate Rewards at a 1:1 ratio or Marriott Bonvoy at a 3:1 ratio. You can also rack up MileagePlus miles through the United℠ Explorer Card.

When booking a flight, you can choose between economy and first class. Based on our research, economy fares typically start at 12,500 miles each way, and first-class tickets go as low as 44,000 miles each way. Both nonstop and connecting flights are available through the airline.

To book a flight on United, head to the airline’s website and enter your dates, airport of origin, and destination. Then click on the box to book with miles.

In order to see the best award availability, the airline recommends you log into your MileagePlus account. If you don’t have one, sign up before you continue the process. From there, you can view mileage requirements for your specific dates — or if you’re flexible, you can check other flights within a few days before and after your chosen dates.

These credit cards could get you to Chicago faster

If you’re planning a trip from LAX to Chicago, credit card rewards can make your trip much more affordable. Here are five cards that should be on your radar as you search for the right one.

Chase Sapphire Reserve®

The Chase Sapphire Reserve® offers the chance to earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. Plus, you'll get 5X points on flights and 10X points on hotels and car rentals when you purchase travel through Chase Ultimate Rewards® immediately after the first $300 is spent on travel purchases annually; 3X points on other travel and dining & 1X points per dollar on all other purchases.

What makes the card so valuable, though, is its flexibility. If you book your Chicago trip through Chase’s portal, you’ll get 50% more value. But you can also transfer your points at a 1:1 value to Southwest, United, and several other airlines, as well as a few hotel rewards programs.

The card has a $550 annual fee, but it makes up for this with several perks, including:

  • A $300 annual travel credit
  • Complimentary airport lounge access through Priority Pass Select
  • An application fee credit for TSA PreCheck or Global Entry
  • Monthly $5 credit to DoorDash and at least a year of complimentary DashPass subscription
  • Two free years of Lyft Pink All Access (activate by Dec. 31, 2024)
  • Complimentary benefits with select hotel brands and car rental programs
  • Various trip protections

If you like the card’s rewards program but aren’t sure about the annual fee, consider the Chase Sapphire Preferred® Card instead. And if you’re a small business owner, the Ink Business Preferred® Credit Card may be a good fit.

American Express® Gold Card

The American Express® Gold Card is an incredible choice if you spend a lot on dining and at U.S. supermarkets. The card offers 4X Membership Rewards points at U.S. supermarkets (up to $25,000 per year, after that 1X) and at restaurants, plus takeout and delivery in the U.S., 3X on flights booked directly with airlines or on, and 1X on all other eligible purchases.

Earn 60,000 Membership Rewards points after you spend $4,000 on eligible purchases within the first 6 months of card membership of account opening. The card charges a $250 annual fee, but it also comes with dining credits of up to $120 each year. (Note that the dining credit benefit requires enrollment.)

American Express Membership Rewards points aren’t too valuable if you redeem them directly with Amex. But if you transfer your points to one of Amex’s transfer partners, including Delta and JetBlue, you may be able to squeeze more value out of each point.

If you want to earn Membership Rewards points and prefer more travel-related perks, consider The Platinum Card® from American Express instead.

The bottom line

Flying from LAX to Chicago doesn’t have to be complicated. But if you want to get there for next to nothing and use as few points or miles as possible, a little research might be needed to make it happen.

While airline-branded credit cards can make it easy to rack up frequent-flyer miles, they restrict you to redeeming your rewards with just one airline. Unless you’re a loyal customer who wants airline perks like priority boarding and free checked bags, consider getting a general travel credit card with multiple airline transfer partners.

This will not only increase your flexibility when trying to find a flight from LAX to Chicago — or anywhere else, for that matter — but also make it easier to earn rewards faster. Whether you’re flying first class or economy, these cards can help get you there.

Easy-to-Earn Unlimited Rewards

Bank of America® Travel Rewards credit card


Card Details

  • Earn 25,000 online bonus points after you make at least $1,000 in purchases in the first 90 days of account opening - that can be a $250 statement credit toward travel purchases
  • Earn 1.5 points per $1 spent on all purchases
  • Longer intro APR on qualifying purchases and balance transfers
  • No foreign transaction fees
  • Apply Now
  • Earn unlimited 1.5 points per $1 spent on all purchases, with no annual fee and no foreign transaction fees and your points don't expire.
  • 25,000 online bonus points after you make at least $1,000 in purchases in the first 90 days of account opening - that can be a $250 statement credit toward travel purchases.
  • Use your card to book your trip how and where you want - you're not limited to specific websites with blackout dates or restrictions.
  • Redeem points for a statement credit to pay for travel or dining purchases, such as flights, hotel stays, car and vacation rentals, baggage fees, and also at restaurants including takeout.
  • 0% Introductory APR for 18 billing cycles for purchases, and for any balance transfers made in the first 60 days. After the intro APR offer ends, 17.99% - 27.99% Variable APR will apply. A 3% fee applies to all balance transfers.
  • If you're a Preferred Rewards member, you can earn 25%-75% more points on every purchase. That means instead of earning an unlimited 1.5 points for every $1, you could earn 1.87-2.62 points for every $1 you spend on purchases.
  • Contactless Cards - The security of a chip card, with the convenience of a tap.
  • This online only offer may not be available if you leave this page or if you visit a Bank of America financial center. You can take advantage of this offer when you apply now.
Apply Now

on Bank of America’s secure website

Read Card Review

Intro Offer

Earn 25,000 online bonus points after you make at least $1,000 in purchases in the first 90 days of account opening - that can be a $250 statement credit toward travel purchases

Annual Fee



Why we like it

Author Details

Ben Luthi Ben is a personal finance and travel writer who loves helping people achieve their money goals. Along with FinanceBuzz, his writing has also been featured on U.S. News, NerdWallet, Experian, Credit Karma, and more.