Chanye previously wrote a trip report on Niagara Falls from the perspective of a credit card/points enthusiast. This time, we’ll continue the series by looking at how to plan a trip to Chicago using credit cards and points.

Chicago attractions overview

Chicago, in Illinois, sits along Lake Michigan and is the third-largest metropolitan area in the US after New York City and Los Angeles. It is the birthplace of McDonald’s, popcorn, the zipper, and roller skates. Most major attractions are along Michigan Avenue. The northern section, also known as the Magnificent Mile, is a street comparable to the Champs-Élysées and is a great area for dining, shopping, and staying. To the south is the Loop, Chicago’s business and tourism center, home to many attractions such as the Art Institute of Chicago, Cloud Gate, Millennium Park, the Field Museum, Willis Tower, and more.

For attraction passes, you can choose City Pass (covering 5 attractions) or Go City Card (all-inclusive or build-your-own). When buying online, don’t forget to use a portal, which can earn a solid amount of cashback (5%-10%). For more itinerary-planning and booking tips, see the Niagara Falls trip report.

Planning flights to Chicago

Chicago has two airports: O'Hare International Airport (ORD) and Midway International Airport (MDW). They are about 20mile and 10mile from downtown, respectively, and both are directly connected to downtown by rail. ORD is a Hub for UA and AA, with lots of flights, so award availability is generally easier to find, and cash fares can also be quite cheap. MDW is a Hub for Southwest and also has plenty of flights. Southwest itself is a low-cost carrier, so fares are inexpensive, and it also includes free checked bags, making it a great option as well.

Award tickets

If you’re traveling during peak season and fares are especially expensive, using miles for flights to Chicago should be one of your first options. ORD is a Hub for AA and UA, and it also has a smaller Delta presence (with nonstop service to ATL, DTW, MSP, LGA, SLC, SEA). MDW, meanwhile, is a Hub for Southwest.

  • AA flights: You can redeem BA miles for them. Since Chicago is in the US Central Time Zone, distances to many destinations work out quite well. If you can’t find a suitable AA nonstop and have to connect, then using AA miles may be a better choice.
  • UA flights: There are plenty of UA flights as well, and redeeming either UA miles or AC miles can be a good deal.
  • Delta flights: Since Delta uses dynamic pricing, sometimes you can find very high-value redemptions.
  • Southwest flights: Award prices are directly tied to cash fares, so if the cash price looks reasonable, you can simply redeem points instead.

Booking flights with points

When overall airfare is relatively cheap, booking flights through bank points is often better value than redeeming airline miles. You also don’t have to worry about award availability, and you can still earn some miles on the ticket.

Use cards with annual travel credits to buy airfare

Using cards with annual travel credits to buy flights can be your first choice, since those credits expire on a schedule and it’s better to use them early rather than keep thinking about them. These are mainly premium cards; for a comparison, see here. Examples include the Chase Sapphire Reserve $300 travel credit, the Citi Prestige $250 travel credit, the US Bank Altitude Reserve $325 travel credit, the AMEX Platinum $200 airline incidental credit, the AMEX Hilton Aspire $250 airline incidental credit, and the AMEX Gold Card $100 airline incidental credit.

Companion tickets (for two travelers)

Companion tickets also usually come with expiration constraints. As long as you can get good value from them, they can be prioritized even ahead of the annual travel-credit cards mentioned above.

  • Southwest companion ticket: If you have a Southwest companion ticket, it’s often a no-brainer, essentially making the airfare half price. One thing to keep in mind is that Southwest in Chicago flies only to MDW, not the more familiar ORD. In addition, Southwest offers free checked bags and free cancellations. Gift cards can also sometimes be bought at a discount on Amazon or other websites.
  • AA companion ticket: This used to be available from the signup bonus on the Barclays Aviator Red, or by spending $20,000 annually on the card. However, you still need to pay an additional $99+tax. For longer trips, it can still provide solid value.
  • Delta companion ticket: The AMEX Platinum Delta SkyMile gives one Delta companion ticket each year. The cost is roughly the annual fee ($195) plus the tax on the second ticket. For longer trips, it can still be worthwhile.
  • Alaska companion ticket: The BofA Alaska Airline gives one Alaska companion ticket each year. The cost is roughly the annual fee ($75)+$99+$22tax. For longer trips, it can still be worthwhile, though it’s generally a better deal for flights to Hawaii.

Buying airfare with a credit card

Once you’ve used up the time-sensitive options above, the remaining route is to pay cash. For specific rewards rates, see this comparison of travel credit cards. If you care about trip delay insurance, reimbursement generally only kicks in after a delay of 6 hours or more, but domestic flights usually don’t get delayed that long.

Airport lounges

At Chicago airports, PPS only has two lounges in Terminal 5, the international terminal. Domestic flights are generally in Terminals 1-3, so the main lounge option is using AMEX Platinum to access a Delta lounge when flying Delta.

Getting around the city

A quick note on local transportation: the subway system is very convenient, so there’s basically no need to rent a car, and parking is also a significant daily expense. If you need to take Uber, it’s not too expensive either, and you can make use of the AMEX Platinum $200 Credit (though of course that is already baked into the annual fee).

Chicago hotels

In general, when booking hotel stays, use FN first (since it expires), then points, and finally consider paying cash either through the hotel’s official website (combined with seasonal promotions) or booking through Hotels (the Hotels option KUKU introduced). For hotel chains, prioritize the one where you have higher elite status. Assuming you’re like me and only have status granted by credit cards, then the order is Hilton>Marriott=Hyatt.

Hyatt

There are 9 hotels in downtown Chicago.

Free Night redemptions

Here I’ll only consider Cat1-4 Free Night certificates. In fact, other than Park Hyatt Chicago, which is not eligible, all the others are options: Thompson Chicago Cat4, Hyatt Centric Chicago Magnificent Mile Cat4, Hyatt Regency Chicago Cat3 (with views of the Chicago River), Hyatt Centric The Loop Chicago Cat4, Hyatt Place Chicago/River North Cat4, and Hyatt Place Chicago/Downtown-The Loop Cat4.

Points Redemptions

Since Free Night certificates can be used for Cat1-4 hotels, I generally prefer to save points for higher-category properties. But if you do not have many points, then lower-category hotels with strong value can also make sense.

  • Park Hyatt Chicago Cat6. This was the first Park Hyatt in the world and is located by Hyatt’s Chicago headquarters. Because it opened quite a long time ago, it can no longer really compare with newly opened hotels, but Park Hyatt Chicago still has special significance and is worth experiencing at least once. The location on the Magnificent Mile is very convenient.
  • Hyatt Regency O'hare Chicago Cat2 offers very good value. If you are overnighting in Chicago during a connection, this is a solid option. I stayed here once; the hotel felt a bit dated, but overall it was perfectly fine.

Hilton

There are 28 hotels in downtown Chicago.

Free Night Redemptions

Hilton Free Night certificates can only be used on weekends, for standard rooms on Friday, Saturday, or Sunday nights. For a usage guide, see this article. Since there is no points cap on these certificates, we should try to redeem them at hotels that otherwise require the most points.

  • Waldorf Astoria Chicago costs 95,000 points for a standard redemption. Standard rooms are hard to find on weekdays, but weekends are usually better, and when standard rooms are available you can use an FN here. The location on the Magnificent Mile is extremely convenient. However, there is no lounge and no free breakfast. Diamond benefits are a $15 daily dining credit per person, which can be used at the first-floor cafe or the third-floor restaurant. Apparently there is also a special service where you can reserve Mercedes transportation within 5 miles of the hotel.
  • Conrad Chicago costs 80,000 points for a standard redemption. Similarly, standard rooms are hard to find on weekdays, but on weekends it is still possible to use an FN here. It is also on the Magnificent Mile, not far from the WA. Compared with the WA, this one should have a lounge and breakfast.

As I said before, if you can redeem for Waldorf Astoria Chicago, don’t overthink the other options.

Points

Compared with the excellent value often possible when redeeming Hilton points for hotels in China, in the US you can usually get only about 0.3 cent or 0.4 cent per point, which is not especially attractive.

Marriott

Marriott also has quite a few hotels here.

Free Night Redemptions

Marriott Free Night certificates come in three tiers: the 50k FN from the AMEX Marriott Bonvoy Brilliant (formerly SPG Luxury) and Chase Ritz-Carlton (discontinued); the 35k FN from the AMEX Marriott Bonvoy (formerly SPG, now discontinued) and Chase Marriott Bonvoy Boundless (formerly Marriott Premier Plus); and the 25k FN from the stay-two-get-one-newbie offer.

For the 50k FN, there is only one real choice.

There are too many options for the 35k FN, with roughly 20 hotels to choose from, so I won’t list them one by one here. For the 25k FN, there are also 7 hotels in downtown Chicago.

FHR

These hotels are all located along both sides of the Magnificent Mile.

  • The Langham, Chicago
  • Four Seasons Hotel Chicago
  • Trump International Hotel & Tower Chicago
  • The Peninsula Chicago
  • Lowe's Chicago Hotel
  • Waldorf Astoria Chicago
  • Park Hyatt Chicago

My Experience (by ymlulu)

Chicago was probably the first city I visited after I started getting into credit cards and points. Later on, I also helped plan a Chicago trip for my parents, so I’ve built up a fair amount of experience.

Flight Options

My first trip to Chicago was for an academic conference. At the time, BA’s lowest-distance award tier covered flights under 650 miles and cost only 4,500 BA miles, which worked out to about $60 in cash value. I checked and found that Tulsa, a somewhat farther nearby city, was only 580 miles from Chicago, while OKC to ORD, despite being geographically closer, was 693 miles. I used gcmap.com to check.

So on a whim, instead of using OKC airport, which was only about a half-hour drive away, I went with ld and drove 3 hours to TUL airport to catch the flight. I still remember leaving at 3 a.m., grabbing a bottle of coffee, and driving straight to the airport. Then we left the car with a friend in Tulsa and rushed off to catch a 7 a.m.-something flight. Looking back, I really had a lot more energy when I was younger. These days I would absolutely pick the easiest option without hesitation.

The second time, when I was planning the trip for my parents, BA had already changed its award rules. So I just had them fly directly from OKC to ORD, again using BA, since for a nonstop it was still much better value than spending 12,500 AA miles.

Hotel Arrangements

My first trip to Chicago was for an academic conference at the Hilton Palmer House. The hotel is in downtown, and the interior is extremely grand. It’s also very convenient for getting around the city center.

At the time, the plan was to attend the conference in Chicago for 2 days and then stay a few extra days for sightseeing. Since I had only recently started getting into points and miles and didn’t have any Hilton points yet—only SPG points—I chose to book a Sheraton near ORD. I redeemed points for 4 nights and got the 5th night free. Every day, I took the hotel’s free shuttle to the airport and then rode the train from the airport into downtown to explore. Looking back, I kind of regret that choice: I wasted more than an hour commuting every day, and it would have been much easier to just stay downtown.

The second time, when I booked for my parents, I already had plenty of Hilton points, so I directly booked the Hilton Palmer House mentioned above and used the stay 4 nights, get the 5th night free benefit. My parents were very satisfied with the stay. However, Hilton was only offering a continental breakfast at the time, and my parents didn’t really know what to make of it, so they ended up going to McDonald’s every day...

Sightseeing and transportation

The first time I visited Chicago, I spent most of my time downtown: checking out the architecture and browsing the upscale shops along the Magnificent Mile, even though I couldn’t really afford anything there anyway. I also went to Navy Pier and rented a bike from the subway station to ride over there, which was quite pleasant. I stopped by Chinatown for some Sichuan food as well. On the last day, I also visited the Chicago zoo. For transportation, I relied entirely on the subway and buses, and I bought a public transit pass that covered everything. After around 7 p.m., there seemed to be more Black people in downtown, so I hurried back to the hotel by train.

The second time, I bought a CityPASS for my parents and arranged visits to various attractions. Later, they said the 5-day itinerary was too packed and not especially worthwhile.

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