Thanksgiving in Chicago: How We Made It a Points-Powered Family Trip
Virgin Atlantic miles, Hyatt free night certificates, and a family reunion worth every redemption.
Some trips you plan purely for the destination. This one was about the people. My oldest daughter Berkley recently started grad school at Northern Illinois University in DeKalb, and Thanksgiving felt like the perfect excuse to get out there, explore Chicago with her and Dom, and see their new home. What made it even sweeter was that the whole trip came together on points and miles, keeping our out-of-pocket costs far lower than you would expect for a five-person holiday weekend.
Here is how we booked it, what it actually cost in points, and what I would do differently next time.
Getting There: SLC to ORD on Delta (Booked Through Virgin Atlantic)
We flew Delta nonstop from Salt Lake City to Chicago O'Hare the day before Thanksgiving, five passengers total. The cash price was $290 per person one way. Through Delta's own website, the same flight cost 22,000 SkyMiles each. But here is where it gets interesting.
Virgin Atlantic is a transfer partner of Chase Ultimate Rewards, and they price Delta metal on a different award chart that often comes in significantly cheaper. The same flight was only 16,500 Virgin Atlantic points per person. Better still, Chase was running a 40% transfer bonus to Virgin Atlantic at the time, which effectively brought the cost down to around 11,800 points per person after the bonus. For five passengers both ways, I transferred approximately 59,000 Chase points for the outbound leg and repeated the process for the return. That is roughly half what Delta would have charged in their own currency for the exact same seat on the exact same plane.
One booking habit I always follow with award travel: book one way rather than round trip. It costs the same in points, and it gives you far more flexibility to cancel or rebook one leg independently if your plans change. With five people traveling, that flexibility matters.
The flights were smooth and on time, which honestly exceeded my expectations for a pre-Thanksgiving travel day. If you are flying out of SLC during a holiday, get there early. We dropped the car at The Parking Spot well before departure, and the shuttle to the terminal was quick and easy. Off-site parking at SLC runs roughly $10 to $15 per day and is consistently more affordable than the airport garage. I always use my Chase Ink Business Preferred when I reserve which give 3x points on travel.
Where We Stayed: Hyatt Regency Chicago
The Hyatt Regency Chicago at 151 East Wacker Drive was where the World of Hyatt program did its heaviest lifting. The hotel sits right on the Chicago River, steps from the Riverwalk, the Magnificent Mile, and virtually every attraction worth visiting downtown. For a points redemption, location is part of the value, and this one is hard to argue with.
The rooms were recently renovated, clean, and comfortable, with great views of either the river or the city skyline. The Regency Club lounge was a genuine perk, especially over a holiday weekend when you want flexibility around meals without the expense of eating out every time. Breakfast at the hotel was solid and saved us from scrambling for a table on Thanksgiving morning when many restaurants were running limited hours.
The Hyatt Regency Chicago is a Category 4 property, which normally runs 15,000 points per night on a standard award. Since I needed two rooms, this was the perfect opportunity to use two World of Hyatt free night certificates instead of burning a large points balance. If you hold the World of Hyatt credit card, those annual free night certificates are one of the most straightforward values in the hotel loyalty space. Redeeming them at a well-located urban property on a holiday weekend is exactly the right move.
Thanksgiving Day: Wicked and Dinner on the River
Thursday was the heart of the trip. We saw Wicked: For Good at the AMC River East theater, and having all four daughters together for it on Thanksgiving made it one of those afternoons I will not forget. If you loved the first film and have not seen the sequel yet, make the time.
After the movie, we had dinner at McCormick and Schmick's Seafood and Steaks at 1 East Wacker, which is practically around the corner from the hotel. The food was excellent and no rideshare was needed. The lesson here is simple: if you are planning a holiday dinner in a major city, lock in your restaurant reservation the same day you book your hotel. Good tables on Thanksgiving disappear fast.
Friday: Chicago, DeKalb, and Berkley's World
Friday morning we started at the Christkindlmarket in Chicago, the open-air German Christmas market held in the city center. The line to get in was long and it was genuinely cold standing outside waiting, but once we were in, it was worth it. The market is charming in a way that felt familiar to us from the Christmas markets we visited on a European river cruise a few years back. Same mulled warmth, same wooden stalls, same sense that someone put real care into the thing. If you go, dress for the cold and go early to beat the crowd.
From there we drove out to DeKalb, home of Northern Illinois University, about 90 minutes west of the city. This leg of the trip was the whole point. We toured Berkley's campus, got a feel for her program, and saw the home she and Dom are building together. There is something grounding about that, seeing the actual place rather than just hearing about it. It stops being abstract.
They took us to Omi Sushi for dinner, a local spot they clearly love, and it earned that loyalty. Everyone left full and happy. Eating somewhere a local chooses for you will beat anything a travel app recommends, and this was no exception.
The rental car through Avis made the DeKalb drive easy for five people. That said, if your Chicago trip stays downtown the whole time, skip the car. Chicago's transit is excellent and the Hyatt Regency puts you within walking distance of almost everything worth doing.
The Return: ORD Back to SLC
We flew home Saturday on Delta, booked the same way as the outbound, through Virgin Atlantic with Chase points transferred at the bonus rate. The flight home was smooth, and we landed in Salt Lake City with enough daylight left to make the drive home feel easy. We picked up the car at The Parking Spot and were back by early evening.
A note on O'Hare post-Thanksgiving: give yourself more time than you think you need. The Saturday after Thanksgiving is one of the busiest travel days of the year, and Terminal 5 is manageable but not fast. We had no issues, but this is not the day to miscalculate your buffer.
The Points and Miles Breakdown
Here is how the key redemptions shook out:
Flights (SLC-ORD-SLC, 5 passengers): Booked through Virgin Atlantic using Chase Ultimate Rewards points transferred at a 40% bonus. Cost: ~11,800 Virgin Atlantic points per person per direction, versus 22,000 Delta SkyMiles through Delta directly.
Hotel (Hyatt Regency Chicago, 2 rooms): Covered with two World of Hyatt free night certificates. Standard award rate is 15,000 points per night at this Category 4 property.
Airport parking (The Parking Spot, SLC): Cash, roughly $10-15 per day.
Car rental (Avis, O'Hare): Cash. Useful for the DeKalb day trip; unnecessary if staying downtown the entire time.
Movie tickets (AMC River East): AMC Stubs points or A-List membership can offset this cost.
The flights and hotel were the headline wins. Paying cash for five people on flights over Thanksgiving weekend would have been painful. A centrally located Chicago hotel during a holiday commands premium nightly rates. Using points for both shifted the real spending to food, the rental car, and parking, which is a fundamentally different budget conversation.
What I Would Do Differently
Watch for transfer bonuses before moving points. The 40% Chase to Virgin Atlantic bonus on this trip was the difference between a good deal and an exceptional one. I keep a loose eye on transfer bonus promotions year-round, and this is a case where patience paid off. If there had been no bonus, the redemption was still better than booking through Delta directly, but the bonus made it nearly half the cost.
Always book award flights one way. It costs the same in points and gives you the ability to cancel or modify each leg independently. When you are moving five people, that flexibility is not theoretical, it is essential.
Book Hyatt award nights early for holidays. Standard award availability at popular urban properties gets picked over quickly once the holiday season approaches. I booked well in advance and had no issues, but this is not a last-minute redemption category.
The Bottom Line
This trip is a clear example of what the points and miles game is actually for. It is not about optimizing for its own sake. It is about making a trip like this one financially realistic, being able to bring the whole family, stay somewhere great, and not spend the whole weekend doing the math on whether you can afford it.
Spending Thanksgiving in Chicago with all four daughters, seeing where Berkley and Dom are building their life, walking the Riverwalk, sitting down for a proper holiday dinner together, that is the return on investment no spreadsheet captures. The Hyatt Regency delivered on every front. The Virgin Atlantic booking strategy saved us an enormous number of points. And DeKalb, a town I would never have visited otherwise, turned out to be exactly the kind of place worth seeing when someone you love calls it home.
If you have Chase points sitting idle and a family member in a city worth visiting, this playbook is worth running. Transfer to Virgin Atlantic when there is a bonus. Book Delta metal. Stay somewhere on the river. Build the trip around the people. Chicago delivered, and we will be back.
