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.
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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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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.
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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.
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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.
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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.
