Chicago had long been on my travel wish list, but I never made it there. This time, my parents also said they wanted to visit, so we finally locked in the trip: 4 adults and 1 child for 5 days and 4 nights (my LD did 4 days and 3 nights and left a day early). Over time, I had built up quite a stash of credit card points and free night certificates, so for this trip I tried to redeem as much as possible and put together a “free” trip to Chicago.

Flights and Airport Lounges

Outbound (SEA-ORD)

  • 5 people, United Economy. Since I had the Chase Sapphire Reserve, I booked directly at 1.5 cents per point using UR points.

I could find UA award tickets, but because departure was less than 21 days from booking, there was a $75/person close-in fee, so I chose to book through UR points at 1.5X instead. Also, without a UA credit card, UA Basic Economy annoyingly did not allow carry-ons, so I had to pay an extra $30/person to upgrade to regular economy. After booking, I realized it actually wasn’t necessary to upgrade all 5 tickets, since we only had 2 carry-on suitcases total. I could have split them into two separate bookings.

There are quite a few lounges at SEA. We went to The Club at SEA, which was fairly close to the UA gate.

Return (ORD-SEA)

1 person, Delta Basic Economy, purchased using a Delta gift card plus reimbursement from the Amex Platinum airline incidental credit. Successfully triggered the Platinum airline reimbursement.

4 people, AA Basic Economy. Since I had a Citi AA credit card, there was no need to upgrade, and the fare was not expensive, so I also booked directly with UR points at 1.5X.

Hotels

Hyatt Regency O’Hare Chicago

10/12-10/13, Hyatt Regency O’Hare Chicago, redeemed 2 rooms at 8000 points/night, for a total of 16,000 Hyatt points.

At check-in, I was told that weekend was Member Appreciation weekend, so all members received lounge access. I had Explorist status matched from Mlife (details here), though the Discoverist status from the Chase Hyatt credit card would have been enough as well.

The hotel hardware was definitely a bit dated, but it was well maintained, and the service was very good. The lounge was not large and food options were limited, but everything tasted pretty good, and there were alcoholic and non-alcoholic drinks as well. It covered our late-night snack that evening and breakfast the next morning. There is a shuttle to and from the airport. If you plan to take the Blue Line into downtown, tell the driver and they can stop at Rosemont Station, where the train fare is 2.5 per ticket; if you depart from O'Hare instead, it is $5 per ticket. Overall, this airport hotel offered very good value.

Residence Inn Chicago Downtown/Loop

10/13-10/15, Residence Inn Chicago Downtown/Loop, redeemed 2 rooms for 2 nights at 35,000 points/night, for a total of 105,000 Marriott points + 1 Cat 5 free night certificate.

I mainly chose this property because of its high rating and relatively new condition, but breakfast and service were both pretty average, perhaps because it had been sold out the day before. The room type was only a studio suite with no upgrade, but the space was large and the decor was indeed fairly new.

Renaissance Chicago Downtown Hotel

10/15-10/16, Renaissance Chicago Downtown Hotel, redeemed 1 room for 1 night at 40,000/night, for a total of 40,000 Marriott points (35,000 two queens + 5,000 upgrade river view).

I had Gold status from an AMEX credit card. I asked about lounge access but was denied; they said the hotel was full, so they could not offer it, though it would normally be possible when occupancy is lower. I was glad I had added 5,000 points when booking to upgrade to a river-view room, because otherwise an upgrade probably would not have happened. The hotel was renovated in 2015 and has an industrial modern style. The outdoor bar on the 3rd floor has a great view. The room itself was average, and the bed was made more messily than any I’ve seen before—I almost thought housekeeping had not finished. The upgraded river view was beautiful: you could see the two Marina City towers and Trump Tower. Right outside are the Red Line and buses that go directly to Chinatown, and the Blue Line to the airport is only about a 5-minute walk away, so the location was quite good.

Transportation:

We did not rent a car. Since my LD left a day early, we bought 2 Ventra cards (one card can be tapped 7 times, meaning it can be used for up to 7 people traveling together) for the subway and buses. If you are only sightseeing in downtown, there is really no need to buy an unlimited ride pass, since most of the time you can just walk. Bus fare is 2.25 one way, subway fare is 2.5 one way, subway transfers within 2 hours are free, and bus transfers within 2 hours are allowed twice at 0.25 each. You can log in to your Ventra account at any time to check the balance and tap history. The first time you buy a new card, there is a $5 charge, but once you register the account, that $5 is returned to your account. If you buy an unlimited pass, though, that $5 credit may not be very useful.

From Navy Pier to Willis Tower, we took the water taxi for 8/person. It was very convenient and the scenery was great. Once you get off, you can immediately see signs pointing to Willis Tower.

Attractions:

The only paid attractions we did were the architecture river cruise (tickets purchased on Mafengwo) and the Willis Tower observation deck (tickets purchased on Fliggy). The cruise tickets took about 1 hour to process, while the Willis Tower tickets were issued instantly. No printing was needed for either—just show the QR code.

Takeaways:

  1. Before making plans, it’s worth checking whether the city has any major events going on first (maybe I’m the only one who forgets to do this?). This trip happened to coincide with the 2019 Chicago Marathon, one of the six World Marathon Majors. Tens of thousands of people came to Chicago, and prices for all 3-star and 4-star hotels jumped to well over $300-$500/night. Even worse, we waited more than 1 hour just to get into Willis Tower, and then another 1+ hour to step onto the glass ledge. For a family of 5, we were only allowed to stay there for 90 seconds.
  2. Thanks to Bonvoy’s deep inventory, as you can see, aside from the one airport hotel night, all the other stays on this trip were redeemed at Bonvoy properties. I originally also had two IHG free night certificates and some Hyatt points, and I wanted to try some nicer hotels from those programs too. But after searching for quite a while, I couldn’t find a single reward night available from either of them. In sharp contrast, for Bonvoy, most hotels were available for redemption unless they were truly sold out. I won’t even get started on Hilton’s sky-high points prices.
  3. For more on planning a Chicago trip, especially how to redeem points for flights and hotels, see: Chicago Travel Planning (From a Points and Miles Perspective)