Deal alert: Nonstop fares to Chicago starting at $81
Quick summary
Update: Some offers mentioned below are no longer available. View the current offers here.
From its spectacular architecture to its endless array of great food, there are lots of reasons why Chicago makes a great city for a weekend jet-away.
You have even more motivation to visit Chicago this winter because you can book nonstop fares at greatly reduced prices. Some routes are going for as low as $81 round-trip. The fare sale also works in reverse if you live in Chicago, and are looking for a break from the Midwest's chilly temperatures.
Fares from American and United are Main Cabin, which comes with a carry-on and seat assignment. Alaska and Delta's discounted fares are basic economy.
Our friends at Thrifty Traveler first spotted this deal, which they sent out to their premium subscribers first. Non-members can find sale prices by using Google Flights to search for desired routes and dates.
Deal basics
Airlines: Delta, American, United, Alaska
Routes: ATL/AUS/AVL/BOS/CHS/DFW/FLL/IAH/JFK/LGA/LAX/MIA/MSY and other cities to Chicago IL (MDW/ORD)
Cost: Nonstop flights available from $81
Dates: January-October 2022; availability varies by city.
Pay with: The Platinum Card® from American Express for 5x on airfare booked directly with the airline or through American Express Travel (on up to $500,000 on these purchases per calendar year); the Citi Prestige® Card for 5x on airfare; the Citi Premier® Card (see rates and fees) (3x on air travel); Chase Sapphire Reserve (3x on air travel); the American Express® Gold Card for 3x on airfare when booked directly with the airline or through Amex Travel or the Chase Sapphire Preferred Card for 2x on travel — which you could redeem for as little as 13,000 points.
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.
If you live in Miami as I do, you can experience a few days of winter in January for just $81 nonstop from Miami International Airport to Chicago (ORD). This is a United Basic Economy fare, so you don't get a carry-on bag. You can upgrade to Economy for $28, which comes with seat selection and a free carry-on. That's a better move than paying $70 for a checked bag at the Basic Economy tier.
You can book Tampa (TPA) to Chicago in February for just $127 nonstop. This is an American Main Cabin fare, which comes with a free carry-on bag and a seat assignment.
One of the best deals we found in this, er...deal, was from Atlanta (ATL) to Chicago (MDW) in March. This nonstop itinerary costs less than half what it normally sells for. Even better, it's for Delta's basic economy, which, despite more restrictions, does come with a free carry-on. Note that you fly into Chicago-Midway Airport on this route, which is closer to the city than O'Hare.
We found a steal of a deal on American to fly from Nashville (BNA) to Chicago (ORD) in February.
We also found fares from San Francisco (SFO) to Chicago (ORD) in late January at great prices. This nonstop itinerary on Alaska Air for just $113 is more than 50% off usual prices. It's Alaska's Saver tier, which includes a free carry-on though no seat assignment.
Related: 11 activities you must do when visiting Chicago
Maximize your purchase
Don't forget to use a card that earns bonus points on airfare purchases, like The Platinum Card® from American Express for 5x on airfare booked directly with the airline or through American Express Travel (on up to $500,000 on these purchases per calendar year); the Citi Prestige® Card for 5x on airfare; the Citi Premier® Card (3x on air travel); Chase Sapphire Reserve (3x on air travel); the American Express® Gold Card for 3x on airfare when booked directly with the airline or through Amex Travel or the Chase Sapphire Preferred Card for 2x on travel — which you could redeem for as little as 13,000 points.
Bottom Line
Once you book your trip, make sure to pack comfortable footwear. Chicago is a great walking city, and exploring on foot is a wonderful way to take it all in. And of course, bring your best coat and layer up. They don't call it the Windy City for nothing!
Featured Image: Duane Walker for Getty Images