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

May 16, 2022
5 min read
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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.

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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

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(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.

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TPG featured card

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TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards

1 - 5X points
5XGet 5X Membership Rewards® points on flights and prepaid hotels on amextravel.com
1.5XEarn 1.5X points on eligible purchases at US construction material & hardware suppliers, electronic goods retailers and software & cloud system providers, and shipping providers, as well as on purchases of $5,000 or more everywhere else, on up to $2 million of these purchases per calendar year
1X1X points for each dollar you spend on eligible purchases.

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Earn 150,000 points120,000 points
The Points Guy Exclusive Offer: Earn 150,000 Membership Rewards® points after you spend $15,000 on eligible purchases with the Business Platinum Card® within the first 3 months of Card Membership.

Annual Fee

$695

Recommended Credit

670-850
Good, Excellent
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

It's hard to find a card that competes with the mile-long list of benefits that come with the Amex Business Platinum. While it's certainly not the card for the average consumer, a business owner with tons of expenses -- especially related to travel -- will find this card incredibly valuable. This card is similar to the consumer version that Amex offers, but with more business-oriented perks around statement credits and earning rates that are a better fit for business owners.

Pros

  • An up to $100 credit for Global Entry or TSA PreCheck application fee every four to five years
  • Up to $400 annual credit for eligible U.S. Dell purchases (enrollment required)
  • Gold status at Marriott and Hilton hotels (enrollment required)
  • Access to the Fine Hotels & Resorts program and Hotel Collection
  • Extended warranty protection
  • International Airline Program and Cruise Privileges Program

Cons

  • Steep annual fee
  • Difficulty meeting $15,000 welcome offer for smaller businesses
  • Limited high-bonus categories outside of travel
  • The Points Guy Exclusive Offer: Earn 150,000 Membership Rewards® points after you spend $15,000 on eligible purchases with the Business Platinum Card® within the first 3 months of Card Membership.
  • Get 5X Membership Rewards® points on flights and prepaid hotels on amextravel.com, and 1X points for each dollar you spend on eligible purchases.
  • Earn 1.5X points (that’s an extra half point per dollar) on eligible purchases at US construction material & hardware suppliers, electronic goods retailers and software & cloud system providers, and shipping providers, as well as on purchases of $5,000 or more everywhere else, on up to $2 million of these purchases per calendar year.
  • Unlock over $1,000 in annual statement credits on a curation of business purchases, including select purchases made with Dell Technologies, Indeed, Adobe, and U.S. wireless service providers.
  • $200 Airline Fee Credit: Get up to $200 in statement credits per calendar year for checked baggage fees, lounge day passes, and more at one selected airline.
  • $189 CLEAR® Credit: Use your Card and get up to $189 back per year on your CLEAR® membership. CLEAR® is available at more than 50 U.S. airports and stadiums.
  • The American Express Global Lounge Collection® can provide an escape at the airport. With more than 1,400 airport lounges across 140 countries and counting, you have more lounge location options than any other credit card on the market as of 9/2021.
  • $695 Annual Fee.
  • Terms Apply.
Apply for The Business Platinum Card® from American Express
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TPG Exclusive Offer
TPG Exclusive Offer
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards Rate

5XGet 5X Membership Rewards® points on flights and prepaid hotels on amextravel.com
1.5XEarn 1.5X points on eligible purchases at US construction material & hardware suppliers, electronic goods retailers and software & cloud system providers, and shipping providers, as well as on purchases of $5,000 or more everywhere else, on up to $2 million of these purchases per calendar year
1X1X points for each dollar you spend on eligible purchases.
  • Intro Offer
    The Points Guy Exclusive Offer: Earn 150,000 Membership Rewards® points after you spend $15,000 on eligible purchases with the Business Platinum Card® within the first 3 months of Card Membership.

    Earn 150,000 points
    120,000 points
  • Annual Fee

    $695
  • 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
    Good, Excellent

Why We Chose It

It's hard to find a card that competes with the mile-long list of benefits that come with the Amex Business Platinum. While it's certainly not the card for the average consumer, a business owner with tons of expenses -- especially related to travel -- will find this card incredibly valuable. This card is similar to the consumer version that Amex offers, but with more business-oriented perks around statement credits and earning rates that are a better fit for business owners.

Pros

  • An up to $100 credit for Global Entry or TSA PreCheck application fee every four to five years
  • Up to $400 annual credit for eligible U.S. Dell purchases (enrollment required)
  • Gold status at Marriott and Hilton hotels (enrollment required)
  • Access to the Fine Hotels & Resorts program and Hotel Collection
  • Extended warranty protection
  • International Airline Program and Cruise Privileges Program

Cons

  • Steep annual fee
  • Difficulty meeting $15,000 welcome offer for smaller businesses
  • Limited high-bonus categories outside of travel
  • The Points Guy Exclusive Offer: Earn 150,000 Membership Rewards® points after you spend $15,000 on eligible purchases with the Business Platinum Card® within the first 3 months of Card Membership.
  • Get 5X Membership Rewards® points on flights and prepaid hotels on amextravel.com, and 1X points for each dollar you spend on eligible purchases.
  • Earn 1.5X points (that’s an extra half point per dollar) on eligible purchases at US construction material & hardware suppliers, electronic goods retailers and software & cloud system providers, and shipping providers, as well as on purchases of $5,000 or more everywhere else, on up to $2 million of these purchases per calendar year.
  • Unlock over $1,000 in annual statement credits on a curation of business purchases, including select purchases made with Dell Technologies, Indeed, Adobe, and U.S. wireless service providers.
  • $200 Airline Fee Credit: Get up to $200 in statement credits per calendar year for checked baggage fees, lounge day passes, and more at one selected airline.
  • $189 CLEAR® Credit: Use your Card and get up to $189 back per year on your CLEAR® membership. CLEAR® is available at more than 50 U.S. airports and stadiums.
  • The American Express Global Lounge Collection® can provide an escape at the airport. With more than 1,400 airport lounges across 140 countries and counting, you have more lounge location options than any other credit card on the market as of 9/2021.
  • $695 Annual Fee.
  • Terms Apply.