Skip to content

Round-trip fares to Chicago, including summer travel dates, starting at $150

May 16, 2022
5 min read
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.

Chicago is among the country's greatest cities to visit during the summer, which is why we are doing you a favor and alerting TPG readers about round-trip flights to Chicago, starting at $150, including peak summer availability.

For more TPG news delivered each morning to your inbox, sign up for our daily newsletter.

Deal basics

(Photo by Nagehan Demirci/EyeEm/Getty Images)

Airlines: United, JetBlue, American and Southwest
Routes: EWR/BOS/JFK/LGA/IAD/DCA/MIA and others to ORD
How to book: Directly through the airline
Travel dates: July 2022 — March 2023
Book by: 2—3 days

Props to Scott’s Cheap Flights for sending us this deal. Sign up for a Premium membership and get deals up to 90% off, which users can try for free for 14 days or $49 per year. You can also upgrade to the Elite tier for $199 per year and receive all the Premium deals plus premium economy, business-class and first-class alerts.

Sample routes

The good news is that this deal features flights for less than $200 departing from a wide variety of U.S. cities, including:

  • Boston (BOS) starting at $150
  • New Haven (HVN) starting at $158
  • Colorado Springs (COS) starting at $168
  • Minneapolis (MSP) starting at $178
  • Miami (MIA)/New York City (JKF/LGA)/Fayetteville (XNA)/Fort Lauderdale (FLL)/Sioux Falls (FSD) starting at $188
  • Baltimore (BWI)/Washington, D.C. (IAD/DCA) starting at $198

Additionally, you can find fights for slightly more than $200, including from Burlington (BTV) starting at $208, Denver (DEN) starting at $218 and Houston (HOU) starting at $227.

To search for this deal, head to Google Flights and enter your origin city and ORD as your destination. For example, this round-trip, nonstop EWR-ORD flight is just over $200. This flight is a good deal considering the normal price for this route is nearly $300.

However, this particular flight is for a fare on United's basic economy class, which does not include full-sized carry-on luggage.

Read more: Sold-out summer: 31 travel tips to keep your trip on track and on budget

Sign up for our daily newsletter
(Screenshot courtesy of Google Flights)

To get around this, consider upgrading to economy for $60, which would still be approximately $100 cheaper than the other flights available on this day for this route since the same flight on American Airlines starts at $352 for their main cabin.

(Screenshot courtesy of Google Flights)

If you have flexibility with your airports, consider departing from LGA and arriving at MDW to fly Southwest, which offers that route for the same dates for a sweet spot right in the middle of the United and AA fares, at $282.

All things considered, this may actually be the best flight option for New York City-based travelers since all SWA fares include two free checked bags, in addition to two carry-ons, specifically one that fits underneath the seat in front of you and a larger bag for the overhead bin.

(Screenshot courtesy of Southwest Airlines)

Since Google Flights omits Southwest flights in their search engine, I always recommend reviewing their low fare calendar ahead of booking. Flying Southwest over another domestic carrier is particularly useful when the cheapest fare listed omits baggage, which is the case for United's basic economy and JetBlue's Blue Basic and Blue fares.

Related: Memorial Day weekend start of busy summer travel season just 3 weeks away

(Screenshot courtesy of Southwest Airlines)

Maximize your purchase

Don’t forget to use a card that earns bonus points on airfare purchases, such as 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). Check out this post for more 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

(Photo by Mlenny/Getty Images)

Although this deal includes flights for upcoming summer travel, as well as deals through December and into early 2023, this is a particularly good deal for last-minute summer trips since airfares for the summer have continued to increase.

Read more: New technology for TSA could reduce airport wait times this 'sold-out summer'

Featured image by 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.

TPG featured card

NEW BENEFIT! TAKEOFF15!
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
3 / 5
Go to review

Rewards

1 - 3X points
3XEarn 3X Miles on Delta purchases and purchases made directly with hotels.
2XEarn 2X Miles at restaurants worldwide, including takeout and delivery in the U.S. and at U.S. supermarkets.
1XEarn 1X Miles on all other eligible purchases.

Intro offer

Earn 90,000 Bonus Miles50,000 Bonus Miles
Earn 90,000 bonus miles after you spend $4,000 in purchases on your new Card in your first 6 months.

Annual Fee

$250

Recommended Credit

670-850
Excellent/Good
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

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
Apply for Delta SkyMiles® Platinum American Express Card
at American Express's secure site
Terms & restrictions apply. See rates & fees
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
3 / 5
Go to review

Rewards Rate

3XEarn 3X Miles on Delta purchases and purchases made directly with hotels.
2XEarn 2X Miles at restaurants worldwide, including takeout and delivery in the U.S. and at U.S. supermarkets.
1XEarn 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 Miles
    50,000 Bonus Miles
  • Annual Fee

    $250
  • 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.

    670-850
    Excellent/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