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The Best Ways to Fly from New York (LGA) to Chicago (ORD)

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Andrew Kunesh

Andrew Kunesh

Former Content Contributor

Countries Visited: 28U.S. States Visited: 22

Andrew’s a lifelong traveler who puts in over 100,000 miles a year, with over 25 countries, 10 business class products, and 2 airline statuses (United and Alaska) under his belt. Andrew’s worked at Th...
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Edited by: Keri Stooksbury

Keri Stooksbury

Editor-in-Chief

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With years of experience in corporate marketing and as the Executive Director of the American Chamber of Commerce in Qatar, Keri is now Editor-in-Chief at UP, overseeing daily content operations and r...
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Kellie Jez

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Kellie’s professional experience has led her to a deep passion for compliance, data reporting, and process improvement. Kellie’s learned the ins and outs of the points and miles world and leads UP’s c...
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The Best Ways to Fly from New York (LGA) to Chicago (ORD)

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Flights from the Windy City to the Big Apple are plentiful. Currently, 5 domestic airlines operate nonstop service between the cities, with American Airlines, Delta Air Lines, and United Airlines all offering near-hourly services between the 2 cities.

With so many flights between the 2 cities, you’d think that flights would be dirt cheap. Thankfully, this is the case for much of the year; when booking months out, you can usually find flights for under $200 round-trip. However, this isn’t the case when booking last-minute flights, flights during holidays, or business-heavy times like large conventions and trade shows.

Thankfully though, you have plenty of options for redeeming points between the 2 cities at relatively low rates.

So to help you find the best fit for your travel plans and mileage account balances, here’s a run through the best ways to fly from LaGuardia Airport (LGA) to Chicago O’Hare International Airport (ORD), with other New York City airports added to the mix, using miles and points in this article.

Get the Best Flat Rate Value with British Airways Avios

Booking short-haul flights with British Airways Avios can be a great option for flying between New York and Chicago / Image courtesy of BritishAirways.com

British Airways may not be the first airline that comes to mind when you think of domestic U.S. flights, but its loyalty program is one of the best ways to redeem for short- and medium- haul trips within the United States.

All North American flights under 1,151 miles cost just 7,500 British Airways Avios and $5.60 in taxes, and since LGA to ORD clocks in at 733 miles, it’s within this low-tier range.

Of course, British Airways cannot operate domestic flights within the U.S., so with that in mind, you’ll fly the route on Oneworld partner, American Airlines. The airline currently operates non-stop flights between ORG and LGA, John F. Kennedy International Airport (JFK), and Newark Liberty International Airport (EWR).

Don’t have British Airways Avios? Don’t worry; it’s a transfer partner of American Express Membership Rewards, Chase Ultimate Rewards, and Marriott Bonvoy.

Even cooler, you can transfer Iberia Avios to British Airways Avios so long as both accounts have been open for 90 days or longer, so you have plenty of options for booking British Airways awards.

British Airways also has its own co-branded credit card from Chase. The card’s current sign-up bonus is a bit unconventional, though: it awards 4x points per dollar spent on your first $30,000 purchases in the first year of being a cardholder. This means you can earn up to 120,000 Avios in your first year, or, enough for 16 one-way trips between LGA and ORD.

Keep an Eye Out for Delta Promotion Awards

Check for cheap Delta award tickets between LGA and ORD / Image courtesy of Delta.com

Delta may not be a favorite loyalty program, but it frequently offers amazing deals between JFK or LGA and ORD. Award tickets start at just 5,000 Delta SkyMiles®, but will may be higher depending on when you book. This is because Delta’s award tickets are priced dynamically based on passenger load, date of booking, and a number of other factors.

Hot Tip: Delta operates a special shuttle service between LGA and ORD. These flights operate hourly and offer upgraded service with complementary alcoholic beverages and a dedicated security lane.

However, if you’re booking well in advance, you have a good shot at booking a Delta SkyMiles award ticket at a low rate. In doing some research, there were 5,000 mile one-way award tickets when booking three months out. See the screen shot above for an example.

You can earn Delta SkyMiles through Delta’s suite of co-branded American Express credit cards.

Delta SkyMiles® Gold American Express CardTerms Apply / Rates & Fees

Delta SkyMiles® Gold American Express Card

U.P. Rating
The rating for this card has been determined by our own industry experts who know the in's and out's of credit card products. Bonuses, rewards as well as rates and fees are all taken into account. Compensation from the issuer does not affect our rating. We only recommend products we either use ourselves or endorse.

This card provides bonus SkyMiles on all purchases, along with a free bag, priority boarding, and discounted award flights.

Learn More(at Amex's secure site)

Delta SkyMiles® Gold American Express Card

This card provides bonus SkyMiles on all purchases, along with a free bag, priority boarding, and discounted award flights.
Earn 40,000 bonus miles after you spend $2,000 in purchases on your new Card in your first 6 months.
40,000 miles
$480
$0 introductory annual fee for the first year, then $99.
20.99%-29.99% Variable
Upgraded Points credit ranges are a variation of FICO®Score 8, one of many types of credit scores lenders may use when considering your credit cardapplication.
Good to Excellent (670-850)

Frequent Delta flyers will love the Delta SkyMiles® Gold American Express Card. The card offers great benefits that will help save you money, effectively mimics low-level elite status with Delta SkyMiles, and helps you earn miles even faster, all for a low annual fee. Let’s dive into the benefits to see if the Delta Gold card is a good fit for your needs.

Pros

  • New: Card Members get 15% off when using miles to book Award Travel on Delta flights through delta.com and the Fly Delta app. Discount not applicable to partner-operated flights or to taxes and fees.
  • Bonus earning on Delta purchases and U.S. supermarket and worldwide restaurant purchases
  • First checked bag free on Delta flights
  • 20% back on inflight purchases

Cons

  • Moderate annual fee
  • Earn rate for Delta flights is relatively low compared to other travel cards
  • Earn 40,000 bonus miles after you spend $2,000 in purchases on your new Card in your first 6 months.
  • Enjoy a $0 introductory Annual Fee for the first year, then $99.
  • Enjoy your first checked bag free on Delta flights.
  • Card Members get 15% off when using miles to book Award Travel on Delta flights through delta.com and the Fly Delta app. Discount not applicable to partner-operated flights or to taxes and fees.
  • Earn 2X Miles on Delta purchases, at U.S. Supermarkets and at restaurants worldwide, including takeout and delivery in the U.S.
  • Earn 1X Mile on all other eligible purchases.
  • $100 Delta Flight Credit: After you spend $10,000 in purchases on your Card in a calendar year, receive a Credit to use toward future travel.
  • Want even more flexibility? Take up to $50 off the cost of your flight for every 5,000 miles you redeem with Pay with Miles when you book on delta.com.
  • Receive a 20% savings in the form of a statement credit on eligible Delta in-flight purchases after using your Card.
  • No Foreign Transaction Fees.
  • With Send & Split®, you can send money and split your Card purchases with any other Venmo or PayPal user, directly from the Amex App. Enroll today.
  • Terms Apply.

Financial Snapshot

  • APR: 20.99%-29.99% Variable
  • Foreign Transaction Fees: None

Card Categories

Rewards Center

Delta SkyMiles Frequent Flyer Program

Delta SkyMiles® Platinum American Express CardTerms Apply / Rates & Fees

Delta SkyMiles® Platinum American Express Card

U.P. Rating
The rating for this card has been determined by our own industry experts who know the in's and out's of credit card products. Bonuses, rewards as well as rates and fees are all taken into account. Compensation from the issuer does not affect our rating. We only recommend products we either use ourselves or endorse.

Frequent Delta travelers will enjoy this card's bonus categories, benefits, and ability to reach higher levels of elite status.

Learn More(at Amex's secure site)

Delta SkyMiles® Platinum American Express Card

Frequent Delta travelers will enjoy this card's bonus categories, benefits, and ability to reach higher levels of elite status.
Earn 50,000 bonus miles after you spend $3,000 in purchases on your new Card in your first 6 months.
50,000 bonus miles
$600
$250
20.99%-29.99% Variable
Upgraded Points credit ranges are a variation of FICO®Score 8, one of many types of credit scores lenders may use when considering your credit cardapplication.
Good to Excellent (670-850)

The Delta SkyMiles® Platinum American Express Card can be a great option for those seeking additional ways to obtain a higher level of status — or to maintain their current status — with the airline.

A key feature of this card is the ability to earn bonus Medallion Qualification Miles (MQMs) that are essential for earning Delta status. This could help you get closer to earning free flights and other valuable rewards.

Pros

  • New: Card Members get 15% off when using miles to book Award Travel on Delta flights through delta.com and the Fly Delta app. Discount not applicable to partner-operated flights or to taxes and fees.
  • 3x SkyMiles per $1 spent on Delta purchases
  • 3x SkyMiles per $1 spent on purchases made directly with hotels
  • 2x SkyMiles per $1 spent at restaurants and U.S. supermarkets
  • 1x SkyMile per $1 spent on all other purchases
  • Annual companion certificate
  • Complimentary checked bags
  • Global Entry or TSA PreCheck application fee statement credit
  • 20% back on inflight purchases
  • Delta Status Boost
  • Discount on Delta Sky Club visits (Effective 1/1/24, this benefit will no longer be available)

Cons

  • $250 annual fee (rates & fees)
  • Does not earn transferable rewards
  • Earn 50,000 bonus miles after you spend $3,000 in purchases on your new Card in your first 6 months.
  • Receive a Domestic Main Cabin round-trip companion certificate each year upon renewal of your Card. Payment of the government imposed taxes and fees of no more than $80 for roundtrip domestic flights (for itineraries with up to four flight segments) is required. Baggage charges and other restrictions apply. See terms and conditions for details.
  • Enjoy your first checked bag free on Delta flights. Plus enjoy Main Cabin 1 Priority Boarding and settle into your seat sooner.
  • Card Members get 15% off when using miles to book Award Travel on Delta flights through delta.com and the Fly Delta app. Discount not applicable to partner-operated flights or to taxes and fees.
  • Earn 3X Miles on Delta purchases and purchases made directly with hotels.
  • Earn 2X Miles at restaurants worldwide including takeout and delivery in the U.S., and at U.S. supermarkets.
  • Earn 1X Miles on all other eligible purchases.
  • Get access to Delta Sky Club® at a rate of $50 per person per visit for you and up to two guests or immediate family when traveling on a Delta flight from now until 12/31/23. Effective 1/1/24, this benefit will no longer be available.
  • Fee Credit for Global Entry or TSA PreCheck® after you apply through any Official Enrollment Provider. If approved for Global Entry, at no additional charge, you will receive access to TSA PreCheck.
  • Earn 10,000 Medallion® Qualification Miles (MQMs) after you spend $25,000 in purchases on your Delta Platinum Card, up to two times through 12/31/23. Effective 1/1/24, this benefit will no longer be available, and there will be a new way to earn toward Medallion Status with the Card. Learn more at delta.com/skymilesprogramchanges.
  • No Foreign Transaction Fees.
  • $250 Annual Fee.
  • Terms Apply.

Financial Snapshot

  • APR: 20.99%-29.99% Variable
  • Foreign Transaction Fees: None

Card Categories

Rewards Center

Delta Air Lines SkyMiles

BEST FOR DELTA LOUNGES
Delta SkyMiles® Reserve American Express CardTerms Apply / Rates & Fees

Delta SkyMiles® Reserve American Express Card

U.P. Rating
The rating for this card has been determined by our own industry experts who know the in's and out's of credit card products. Bonuses, rewards as well as rates and fees are all taken into account. Compensation from the issuer does not affect our rating. We only recommend products we either use ourselves or endorse.

Delta loyalists will love the fast track to Delta elite status, lounge access, baggage benefits, and upgrade priority with the Delta Reserve card.

Learn More(at Amex's secure site)

Delta SkyMiles® Reserve American Express Card

Delta loyalists will love the fast track to Delta elite status, lounge access, baggage benefits, and upgrade priority with the Delta Reserve card.
Earn 60,000 bonus miles after you spend $5,000 in purchases on your new Card in your first 6 months.
60,000 miles
$720
$550
20.99%-29.99% Variable
Upgraded Points credit ranges are a variation of FICO®Score 8, one of many types of credit scores lenders may use when considering your credit cardapplication.
Good to Excellent (670-850)

The Delta SkyMiles® Reserve American Express Card is a stellar option for frequent travelers who always fly with Delta thanks to its lounge access, status boost, annual companion certificate, and many other great benefits.

Here is a full look at everything the Delta Reserve card can offer to you to help you decide whether the card deserves a place in your wallet.

Pros

  • New: Card Members get 15% off when using miles to book Award Travel on Delta flights through delta.com and the Fly Delta app. Discount not applicable to partner-operated flights or to taxes and fees.
  • 3x SkyMiles per $1 on Delta purchases
  • 1x SkyMile per $1 on all other purchases
  • Complimentary Delta Sky Club and Amex Centurion Lounge access when flying Delta. Effective 2/1/25, Reserve Card Members will receive 15 Visits per year to the Delta Sky Club; to earn an unlimited number of Visits each year starting on 2/1/25, the total eligible purchases on the Card must equal $75,000 or more between 1/1/24 and 12/31/24, and each calendar year thereafter.
  • Delta Status Boost
  • Medallion Qualification Dollar (MQD) Waiver
  • Annual Companion Certificate
  • Access to Complimentary Upgrades and Upgrade Priority
  • Free checked bags
  • 20% back on inflight purchases
  • Global Entry or TSA PreCheck application fee statement credit
  • Travel and purchase protection

Cons

  • $550 annual fee (rates and fees)
  • No bonus categories other than Delta purchases
  • Earn 60,000 bonus miles after you spend $5,000 in purchases on your new Card in your first 6 months.
  • Enter Delta Sky Club® at no cost and bring up to two guests or immediate family at a rate of $50 per person per visit. Effective 2/1/25, Reserve Card Members will receive 15 Visits per year to the Delta Sky Club; to earn an unlimited number of Visits each year starting on 2/1/25, the total eligible purchases on the Card must equal $75,000 or more between 1/1/24 and 12/31/24, and each calendar year thereafter.
  • Enjoy complimentary access to The Centurion® Lounge when you book a Delta flight with your Reserve Card.
  • With Status Boost®, earn 15,000 Medallion Qualification Miles (MQMs) after you spend $30,000 in purchases on your Card through 12/31/23, up to four times per year getting you closer to Medallion Status. MQMs are used to determine Medallion Status and are different from the miles you earn towards flights. Effective 1/1/24, this benefit will no longer be available, and there will be a new way to earn toward Medallion Status with the Card. Learn more at delta.com/skymilesprogramchanges.
  • Eligible Card Members get 15% off when using miles to book Award Travel on Delta flights through delta.com and the Fly Delta app. Discount not applicable to partner-operated flights or to taxes and fees.
  • Receive a domestic First Class, Delta Comfort+® or domestic Main Cabin round trip companion certificate each year upon renewal of your Card. Payment of the government imposed taxes and fees of no more than $80 for roundtrip domestic flights (for itineraries with up to four flight segments) is required. Baggage charges and other restrictions apply. See terms and conditions for details.
  • Fee Credit for Global Entry or TSA PreCheck® after you apply through any Official Enrollment Provider. If approved for Global Entry, at no additional charge, you will receive access to TSA PreCheck.
  • Enjoy your first checked bag free on Delta flights.
  • Earn 3X Miles on Delta purchases.
  • Earn 1X Mile on all other eligible purchases.
  • No Foreign Transaction Fees.
  • $550 Annual Fee.
  • Terms Apply.

Financial Snapshot

  • APR: 20.99%-29.99% Variable
  • Foreign Transaction Fees: None

Card Categories

Rewards Center

Delta SkyMiles Airline Loyalty Program

Further, you can transfer in miles from American Express Membership Rewards and Marriott Bonvoy.

Book United Awards with Avianca LifeMiles

Prefer booking Star Alliance awards? Avianca LifeMiles is your best bet. U.S. domestic routes on United can be booked starting at just 10,000 Avianca LifeMiles.

The airline flies between both LGA and EWR to ORD, giving you plenty of options for transit between the 2 cities. As you’d expect, the taxes and fees are the standard $5.60 each way.

Hot Tip: Have United Airlines elite status? Add your MileagePlus® number to your LifeMiles award ticket and you’ll be eligible for priority seating, upgrades, free checked bags, and other elite status benefits.

You can also transfer Citi ThankYou®, American Express Membership Rewards, and Marriott Bonvoy points to Avianca LifeMiles.

Use JetBlue TrueBlue or Southwest Rapid Rewards points to Cover Cheap Tickets

JetBlue TrueBlue and Southwest Rapid Rewards have surprisingly similar loyalty programs. Both airlines price awards based on how much the paid ticket costs, so if a paid ticket is expensive, so will the award ticket. However, no matter the award cost, you’ll only pay $5.60 in taxes for tickets on either airline.

Booking New York to Chicago on JetBlue

JetBlue TrueBlue miles can be a good option for flying between New York and Chicago. Image courtesy of JetBlue.com

On the JetBlue side, the airline operates flights between JFK and ORD. Unfortunately, there is no EWR or LGA service offered to ORD at this time. You can transfer points from American Express Membership Rewards, Chase Ultimate Rewards, Citi ThankYou, and Marriott Bonvoy to JetBlue.

When booking 3 months out, there were JetBlue tickets between New York and Chicago pricing at around 8,700 points one-way. This puts them a little above a British Airways award ticket, but still makes them a cheaper option than redeeming miles for a flight using American Airlines or United Airlines miles at 12,500 miles one-way.

The same 8,700 point one-way ticket costs $127 when booked with cash. This means you’ll get just under 1.4 cents per point in value for your points, so we don’t recommend transferring Chase Ultimate Rewards miles to book this award. Why? Simple: you can book the ticket through the Chase Travel Portal for less points. More on that later!

Booking New York to Chicago on Southwest Airlines

Using Southwest Rapid Rewards miles can yield great value for flights between New York and Chicago / Image courtesy of Southwest.com

On the other hand, Southwest Airlines flies between LGA and EWR and Chicago Midway International Airport (MDW) multiple times per day. Southwest has a suite of co-branded credit cards with Chase, and points transfer in from Chase Ultimate Rewards and Marriott Bonvoy.

There were flights for just 6,145 miles one-way when booking three months out, with the same paid ticket being $99. This gives you a 1.5 cent per point value for your Southwest points, so like JetBlue, tread lightly if you plan on transferring in points from Chase Ultimate Rewards.

Book with the Chase Travel Portal

Using the Chase Travel Portal can be a good use of miles if booking a cheap paid ticket. / Image courtesy of Chase.com

If you have a Chase credit card that earns Ultimate Rewards, you can redeem your points towards paid flights on virtually any airline that flies between New York City and Chicago. The portal is powered by Expedia and will let you book flights on any ticket that Expedia sells using your Chase Ultimate Rewards points.

However, the cent-per-point value you get from the portal depends on the Chase Ultimate Rewards earning card you have. The Chase Sapphire Reserve® gets 1.5 cents per point towards flights, the Chase Sapphire Preferred® gets 1.25 cents per point, and all other cards get 1 cent per point.

These redemptions may be worthwhile if you want to redeem points for a cheap ticket. For example, a $94.30 one-way ticket on Delta would cost 6,286 Chase Ultimate Rewards points if you have a Chase Sapphire Reserve. This is over 1,000 points less than redeeming points for a similar flight through British Airways.

Further, note that you’ll still earn points when redeeming these flights. This is because Chase essentially pays for a paid ticket for you, so make sure to add your frequent flyer number to any tickets you book through the Chase Travel Portal.

The only downside with booking through the Chase Travel Portal is that you may be losing some point value when compared to using transfer partners. You can often get 2+ cents per point in value when redeeming Chase Ultimate Rewards with transfer partners, so consider your options if you plan on splurging for a more exciting award in the future.

Final Thoughts

In this article, you saw the best ways to redeem miles for flights between New York and Chicago. Generally, stick to British Airways redemptions if possible; this will generally provide the best value, and let you travel between the 2 cities for just 7,500 Avios one-way.

However, remember that these flights can be purchases for cheap if you book far enough in advance. So if time’s on your side, definitely check paid flights first and assess if the price is worth using your points for, or just purchasing the ticket outright.

For rates and fees of the Delta SkyMiles® Gold American Express Card, click here.
For rates and fees of the Delta SkyMiles® Platinum American Express Card, click here.
For rates and fees of Delta SkyMiles® Reserve American Express Card, click here.

Featured Image Credit: stephan cassara via Unsplash

Frequently Asked Questions

What airlines fly between New York and Chicago?

Currently, American Airlines, Delta Airlines, United Airlines, Southwest Airlines, Spirit, and JetBlue fly between New York and Chicago. American, Delta, and United each fly near-hourly shuttle service between the two cities.

How many airports are there in New York City and Chicago?

Currently, there are 3 New York City airports: LaGuardia Airport (LGA), John F. Kennedy International Airport (JFK), and Newark Liberty International Airport (EWR). Chicago has 2 airports: Chicago O’Hare International Airport (ORD) and Chicago Midway International Airport (MDW), with Southwest being the dominate carrier at MDW (and the only serving New York City).

About Andrew Kunesh

Andrew was born and raised in the Chicago suburbs and now splits his time between Chicago and New York City.

He’s a lifelong traveler and took his first solo trip to San Francisco at the age of 16. Fast forward a few years, and Andrew now travels just over 100,000 miles a year, with over 25 countries, 10 business class products, and 2 airline statuses (United and Alaska) under his belt. Andrew formerly worked for The Points Guy and is now Senior Money Editor at CNN Underscored.

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