Deal alert: Nonstop fares to Chicago starting at $81
This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. Terms apply to the offers listed on this page. For an explanation of our Advertising Policy, visit this page.
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.
Want your TPG news delivered straight to your inbox each morning? Sign up for our daily newsletter
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.
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 (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.
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.
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
Welcome to The Points Guy!
Earn 50,000 bonus miles and 5,000 Medallion® Qualification Miles (MQMs) after you spend $2,000 in purchases on your new card in the first three months of card membership. Plus, earn up to $100 back in statement credits for eligible purchases at U.S. restaurants in the first three months of card membership.
With Status Boost™, earn 10,000 Medallion Qualification Miles (MQMs) after you spend $25,000 in purchases on your Card in a calendar year, up to two times per year getting you closer to Medallion Status. Earn 3X Miles on Delta purchases and purchases made directly with hotels, 2X Miles at restaurants and at U.S. supermarkets and earn 1X Mile on all other eligible purchases. Terms Apply.
- Earn 50,000 Bonus Miles and 5,000 Medallion® Qualification Miles (MQMs) after you spend $2,000 in purchases on your new Card in your first 3 months.
- Plus, earn up to $100 back in statement credits for eligible purchases at U.S. restaurants with your card within the first 3 months of membership.
- Earn up to 20,000 Medallion® Qualification Miles (MQMs) with Status Boost® per year. After you spend $25,000 in purchases on your Card in a calendar year, you can earn 10,000 MQMs two times per year, getting you closer to Medallion® Status. MQMs are used to determine Medallion® Status and are different than miles you earn toward flights.
- Earn 3X Miles on Delta purchases and purchases made directly with hotels.
- Earn 2X Miles at restaurants worldwide, including takeout and delivery and at U.S. supermarkets.
- Earn 1X Miles on all other eligible purchases.
- 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 $75 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.
- Fee Credit for Global Entry or TSA Pre✓®.
- Enjoy an exclusive rate of $39 per person per visit to enter the Delta Sky Club® for you and up to two guests when traveling on a Delta flight.
- No Foreign Transaction Fees.
- $250 Annual Fee.
- Terms Apply.
- See Rates & Fees