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Fly to Chicago for as low as $118

Nov. 17, 2022
5 min read
The Chicago, Illinois skyline
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The birthplace of the skyscraper and deep-dish pizza, Chicago is a bustling city with a history and culture of its own that’s worth experiencing. You can experience all Chicago has to offer with flights to the Windy City starting at $118.

BOB KRIST/GETTY IMAGES

Multiple airlines are offering discounted fares to Chicago from cities all over the U.S., and the travel dates are generally from November 2022 to April 2023.

These fares are only expected to last for a couple of days, so we recommend booking your tickets as soon as possible.

Deal basics

Airlines: Alaska Airlines, American Airlines, Delta Air Lines, JetBlue, Southwest Airlines and United Airlines.
Routes: Atlanta, Boston, Dallas, Denver, Houston, Las Vegas, Los Angeles, Miami, Minneapolis, Newark, New York City, Philadelphia, Seattle and other cities to Chicago.
How to book: Use Google Flights to determine your best dates, then book directly with the airline of your choice.
Travel dates: Generally from November 2022 to April 2023.
Book by: The next one to two days.

Kudos to Scott’s Cheap Flights for flagging this deal. To receive discounts of up to 90%, sign up for the site’s Premium membership, which costs $49 a year and comes with a 14-day free trial. Or, sign up for the Elite Tier membership, which also sources premium, business-class and first-class deals.

Sample flights

This deal offers great flexibility — you can fly to Chicago from nearly anywhere in the contiguous U.S., and most fares to the Windy City are less than $200.

Here are some standout flights:

  • American and United: Boston Logan International Airport (BOS) to O’Hare International Airport (ORD), starting at $118.
  • United: Bradley International Airport (BDL) in Connecticut to ORD, starting at $118.
  • American and United: Denver International Airport (DEN) to ORD, starting at $138.
  • United: George Bush Intercontinental Airport (IAH) in Houston to ORD, starting at $138.
  • United and American: Philadelphia International Airport (PHL) to ORD, starting at $138.
  • Southwest: LaGuardia Airport (LGA) in New York to Chicago Midway International Airport (MDW), starting at $158.
  • Alaska, Delta and United: Seattle-Tacoma International Airport (SEA) to ORD, starting at $178.
  • United: Sioux City Gateway Airport (SUX) in Iowa to ORD, starting at $194.

We recommend searching through Google Flights to determine your ideal dates and then booking your flights directly with the airline, because airlines are more dependable in the event your flight faces a cancellation, delay or booking change.

If you’re flying from Hartford on Jan. 31, United has two flights at $118 — one departs at 6 a.m. and the other at 4:51 p.m. For returning flights, United offers one at 6:28 p.m. on Feb. 6 at the same $118 price.

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GOOGLE.COM/FLIGHTS

The fares featured in this bundle of cheap flights only apply to basic economy. United’s basic economy fare does not let passengers bring carry-ons or make changes to their flights. Passengers will also have to pay an additional fee if they want to select a seat. However, for a flight from Hartford to Chicago, which is a little more than two hours, basic economy can be a solid option, since it's the cheapest fare for such a short flight.

UNITED.COM
GOOGLE.COM/FLIGHTS

The $118 price tag for a trip to Chicago is considered to be low, since the cheapest possible flights to Chicago cost anywhere from $215 to $435, according to Google Flights.

GOOGLE.COM/FLIGHTS

As for seat selection, United economy class seats cost between $15 and $21 — the aisle seats are on the more expensive end, whereas middle seats are the cheapest. You can also pay anywhere from $25 to $41 for a United preferred seat which features more legroom.

UNITED.COM

Maximize your purchase

Use cards that earn bonus points on airfare purchases like The Platinum Card® from American Express (5 points per dollar on airfare booked directly with the airline or through American Express Travel), on up to $500,000 on these purchases per calendar year, Citi Prestige® Card (5 points per dollar on airfare), Citi Premier® Card, Chase Sapphire Reserve (3 points per dollar on airfare), American Express® Gold Card (3 points per dollar on airfare when booked directly with the airline or through Amex Travel) or the Chase Sapphire Preferred Card (2 points per dollar on travel). This post has more information on maximizing airfare purchases.

The information for the Citi Prestige 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.

Bottom line

If you’ve ever wanted to visit Chicago, then this deal is definitely worth booking, considering you can even book flights to the city from the West Coast for under $200. Even though the travel dates in this deal take place during some of Chicago’s colder months, you can beat the crowds at many of the tourist attractions. Plus, from ice skating at Millennium Park to visiting the Art Institute of Chicago, there is tons to do, regardless of the season.

Featured image by RAYMOND BOYD/GETTY IMAGES
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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TPG featured card

Best card for premium perks while traveling
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards

2 - 10X points
10XEarn unlimited 10X miles on hotels and rental cars booked through Capital One Travel
5X5X miles on flights booked through Capital One Travel.
2X2 Miles per dollar on every purchase, every day

Intro offer

75,000 bonus miles
Earn 75,000 bonus miles when you spend $4,000 on purchases in the first 3 months from account opening, equal to $750 in travel

Annual Fee

$395

Recommended Credit

740-850
Excellent
Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

Why We Chose It

The Capital One Venture X card is one of the best all-round travel credit cards ever launched. Not only is it offering a tremendous welcome bonus, but cardholders can earn tons of miles on everyday spending and receive a 10,000-mile anniversary bonus to boot. Its annual fee is $395, but cardholders can count on up to $300 in statement credits toward travel booked through Capital One Travel each year and other valuable benefits like access to Priority Pass lounges and Capital One’s own growing family of airport lounges.

Pros

  • Excellent welcome offer worth 75,000 miles after you spend $4,000 on purchases in the first three months.
  • Up to $300 in annual travel statement credits toward bookings make through Capital One Travel.
  • 10,000 bonus miles (worth $100 toward travel) each account anniversary.

Cons

  • The $395 annual fee might be expensive for some, but this card’s benefits provide much more value than that.
  • If you don’t travel frequently, this might not be the best card for you.
  • Earn 75,000 bonus miles when you spend $4,000 on purchases in the first 3 months from account opening, equal to $750 in travel
  • Receive up to $300 back annually as statement credits for bookings through Capital One Travel, where you'll get Capital One's best prices on thousands of options
  • Get 10,000 bonus miles (equal to $100 towards travel) every year, starting on your first anniversary
  • Earn unlimited 10X miles on hotels and rental cars booked through Capital One Travel and 5X miles on flights booked through Capital One Travel
  • Earn unlimited 2X miles on all other purchases
  • Unlimited complimentary access for you and two guests to 1,400+ lounges, including Capital One Lounges and our Partner Lounge Network
  • Receive up to a $100 credit for Global Entry or TSA PreCheck®
  • Use your Venture X miles to easily cover travel expenses, including flights, hotels, rental cars and more—you can even transfer your miles to your choice of 15+ travel loyalty programs
  • Named editors' choice for "Best New Credit Card of 2021" by The Points Guy
  • Earn 10 miles per dollar when you book on Turo, the world's largest car sharing marketplace, through May 16, 2023
Best card for premium perks while traveling
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards Rate

10XEarn unlimited 10X miles on hotels and rental cars booked through Capital One Travel
5X5X miles on flights booked through Capital One Travel.
2X2 Miles per dollar on every purchase, every day
  • Intro Offer
    Earn 75,000 bonus miles when you spend $4,000 on purchases in the first 3 months from account opening, equal to $750 in travel

    75,000 bonus miles
  • Annual Fee

    $395
  • Recommended Credit
    Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

    740-850
    Excellent

Why We Chose It

The Capital One Venture X card is one of the best all-round travel credit cards ever launched. Not only is it offering a tremendous welcome bonus, but cardholders can earn tons of miles on everyday spending and receive a 10,000-mile anniversary bonus to boot. Its annual fee is $395, but cardholders can count on up to $300 in statement credits toward travel booked through Capital One Travel each year and other valuable benefits like access to Priority Pass lounges and Capital One’s own growing family of airport lounges.

Pros

  • Excellent welcome offer worth 75,000 miles after you spend $4,000 on purchases in the first three months.
  • Up to $300 in annual travel statement credits toward bookings make through Capital One Travel.
  • 10,000 bonus miles (worth $100 toward travel) each account anniversary.

Cons

  • The $395 annual fee might be expensive for some, but this card’s benefits provide much more value than that.
  • If you don’t travel frequently, this might not be the best card for you.
  • Earn 75,000 bonus miles when you spend $4,000 on purchases in the first 3 months from account opening, equal to $750 in travel
  • Receive up to $300 back annually as statement credits for bookings through Capital One Travel, where you'll get Capital One's best prices on thousands of options
  • Get 10,000 bonus miles (equal to $100 towards travel) every year, starting on your first anniversary
  • Earn unlimited 10X miles on hotels and rental cars booked through Capital One Travel and 5X miles on flights booked through Capital One Travel
  • Earn unlimited 2X miles on all other purchases
  • Unlimited complimentary access for you and two guests to 1,400+ lounges, including Capital One Lounges and our Partner Lounge Network
  • Receive up to a $100 credit for Global Entry or TSA PreCheck®
  • Use your Venture X miles to easily cover travel expenses, including flights, hotels, rental cars and more—you can even transfer your miles to your choice of 15+ travel loyalty programs
  • Named editors' choice for "Best New Credit Card of 2021" by The Points Guy
  • Earn 10 miles per dollar when you book on Turo, the world's largest car sharing marketplace, through May 16, 2023