Deal alert: Nonstop fares to Chicago starting at $81
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.
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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 (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
Top offers from our partners
How we chose these cards
TPG featured card
Rewards
| 3X | Earn 3X Miles on Delta purchases and purchases made directly with hotels. |
| 2X | Earn 2X Miles at restaurants worldwide, including takeout and delivery in the U.S. and at U.S. supermarkets. |
| 1X | Earn 1X Miles on all other eligible purchases. |
Intro offer
Annual Fee
Recommended Credit
Why We Chose It
Build your loyalty to Delta by applying for the carrier's mid-tier card option, the Delta SkyMiles Platinum card. The annual fee is quickly recouped by the card's travel perks, such as an application credit to Global Entry or TSA Precheck, annual companion certificate and so much more. Plus you can fast-track to elite status simply through card spend.Pros
- Earn bonus Medallion® Qualification Miles (MQMs) and an Medallion Qualifying Dollar (MQD) waiver when you hit specific spending thresholds with your card within a calendar year
- Receive a Domestic Main Cabin round-trip companion certificate each year
- Statement credit for TSA PreCheck/Global Entry fee (up to $100)
- First checked bag free
Cons
- Doesn't make sense if you don't fly Delta
- SkyMiles aren't the most valuable airline currency
- Earn 90,000 bonus miles after you spend $4,000 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.
- 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.
- 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 Mile on all other eligible purchases.
- Enjoy a per-visit rate of $50 per person for Card Members and up to two guests to enter the Delta Sky Club when traveling on a Delta flight.
- Fee Credit for Global Entry or TSA PreCheck® after you apply through any Authorized Enrollment Provider. If approved for Global Entry, at no additional charge, you will receive access to TSA PreCheck.
- 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 up to 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.
- No Foreign Transaction Fees.
- $250 Annual Fee.
- Terms Apply.
- See Rates & Fees
Rewards Rate
| 3X | Earn 3X Miles on Delta purchases and purchases made directly with hotels. |
| 2X | Earn 2X Miles at restaurants worldwide, including takeout and delivery in the U.S. and at U.S. supermarkets. |
| 1X | Earn 1X Miles on all other eligible purchases. |
Intro Offer
Earn 90,000 bonus miles after you spend $4,000 in purchases on your new Card in your first 6 months.Earn 90,000 Bonus Miles50,000 Bonus MilesAnnual Fee
$250Recommended 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.670-850Excellent/Good
Why We Chose It
Build your loyalty to Delta by applying for the carrier's mid-tier card option, the Delta SkyMiles Platinum card. The annual fee is quickly recouped by the card's travel perks, such as an application credit to Global Entry or TSA Precheck, annual companion certificate and so much more. Plus you can fast-track to elite status simply through card spend.Pros
- Earn bonus Medallion® Qualification Miles (MQMs) and an Medallion Qualifying Dollar (MQD) waiver when you hit specific spending thresholds with your card within a calendar year
- Receive a Domestic Main Cabin round-trip companion certificate each year
- Statement credit for TSA PreCheck/Global Entry fee (up to $100)
- First checked bag free
Cons
- Doesn't make sense if you don't fly Delta
- SkyMiles aren't the most valuable airline currency
- Earn 90,000 bonus miles after you spend $4,000 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.
- 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.
- 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 Mile on all other eligible purchases.
- Enjoy a per-visit rate of $50 per person for Card Members and up to two guests to enter the Delta Sky Club when traveling on a Delta flight.
- Fee Credit for Global Entry or TSA PreCheck® after you apply through any Authorized Enrollment Provider. If approved for Global Entry, at no additional charge, you will receive access to TSA PreCheck.
- 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 up to 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.
- No Foreign Transaction Fees.
- $250 Annual Fee.
- Terms Apply.
- See Rates & Fees