Chicago: Food, Fun and Free Nights
Just like our “Before the Blog” post, this trip to Chicago was prior to the site’s conception, so we didn’t keep track of every single detail - but we pulled together enough highlights to give it a proper blog post of its own.
How We Got There
We flew Southwest, but we didn’t have enough Rapid Rewards points to cover the flights - and after checking, the redemption value wasn’t strong enough to justify transferring our Chase points (which is typically the case transferring from Chase to Southwest). That said, we paid cash: $160.51 per person, round trip.
Where We Stayed
When deciding where to stay, we wanted something central, stylish and points-friendly. The Kimpton Gray Hotel, part of the IHG portfolio, checked all the boxes - and we were able to use 3 of the 5 free nights from the IHG One Rewards Premier Credit Card sign-up bonus to cover the stay. You can read more about that card here.
One of the perks of this card is that it comes with automatic IHG Platinum Elite status, which scored us a complimentary room upgrade at check-in. The upgraded room gave us a bit more space and a better view - definitely a nice bonus that made the stay feel more elevated.
The hotel has a boutique feel with modern rooms, a beautiful lobby and a rooftop bar that made for a perfect nightcap. The location in the Loop made it easy to explore the city whether we were heading north toward the Riverwalk or west to grab dinner. For a points-based stay, it felt like a real win - especially because it didn’t cost us any points or cash out of pocket.
What We Did + What We Ate
Day 1: Arrival, Exploring and a Can’t Miss Dinner
After landing in Chicago, we headed to the Kimpton Gray to check in and get settled. Once we dropped our bags, we made our way to grab lunch at Portillo’s - a classic first stop for anyone visiting the city. We each grabbed a Chicago-style hot dog and split an Italian beef sandwich. Both lived up to the hype and made for the perfect casual (and very Chicago) welcome meal.
With some fuel in our system, we spent the afternoon exploring the Magnificent Mile, popping into a few shops and soaking in the energy of the city. On our way back to the hotel, we stopped at the Starbucks Reserve Roastery, a four-story shrine to coffee lovers. Even if you’re not a coffee person, it’s worth checking out just for the architecture and pastries and cocktails that you won’t find at your local Starbucks.
After freshening up, we headed to dinner at Iron Chef Stephanie Izard’s Girl & the Goat - a restaurant recommended to us more than once. The menu has changed since our visit, but we can still taste the highlights: brussels sprouts, roasted asparagus, goat empanadas and a grilled prime skirt steak. The restaurant encourages sharing, which works perfectly for how we like to dine. We’re pretty sure we had dessert, though nothing on the current menu jogs the memory. What we do remember: everything was absolutely delicious. This place easily earned a spot on our “must-return” list.
Day 2: Art, Architecture and Anniversary Dinner
We started the day with breakfast at Beatrix in the Loop. We both ordered the Hazelnut Oat Mocha (highly recommend), and Greg had the Ranchero Breakfast Burrito - which he still insists is the best breakfast burrito he’s ever had. Jen’s order escapes us, but the whole vibe of the place was warm and inviting.
After breakfast, we headed to the Riverwalk for a morning stroll. It was a little early for most of the shops or restaurants to be open, but it made for a relaxing start to the day. From there, we walked over to Millennium Park to see the Cloud Gate - aka The Bean. It’s one of those things that’s fun to see in person, even if you only spend about ten minutes there.
Next up was the Art Institute of Chicago, which was a great way to slow things down and dive into a bit of culture (plus, Jen always loves a good art museum when traveling). We were still full from breakfast, so we skipped lunch and powered through the afternoon.
Later that day, we boarded the Chicago Architecture River Cruise on the First Lady - easily one of the best experiences we had in Chicago. The guide was super knowledgeable and it was fascinating to learn about all the different styles of architecture that line the river. Plus, after all the walking we’d done over the past day and a half, sitting for 90 minutes on a boat felt like a perfect break.
That night, we celebrated our anniversary with a dinner a RPM Steak. Greg started with the RPM Gin & Tonic, which he really enjoyed, and for our entrees, he had the Delmonico Ribeye which Jen went with the Petit Filet. We shared the Japanese Sweet Potatoes - and let us tell you, those along are worth a visit. For desert, we had Martha M’s Special Occasion Carrot Cake, and since we were celebrating, they brought out a signature cotton candy tower. It was a fun touch. Overall, the food was good - but for the price point, we weren’t totally blown away. It’s probably not a place we’d rush back to, but we’re glad we tried it.
Day 3: Vietnamese Favorites, Ferris Wheel Views & Late Night Laughs
We let ourselves sleep in on day three since we knew we had a late night ahead of us and started the day with lunch at Le Colonial. This ended up being our favorite meal of the entire trip. We don’t remember every dish we ordered, but the Bo Luc Lac (Shaking Beef) and Bo State (State Spiced Filet Mignon) were both incredible. Every bite was full of rich flavor, and the atmosphere was elegant without being too formal. 10/10.
After lunch, we headed to Navy Pier and took a ride on the Ferris Wheel. The views from the top were beautiful and gave us a fresh appreciation for just how scenic Chicago really is - especially with the city skyline reflecting off the lake.
Dinner that night was at Chicago Q, a barbecue spot that we had high hopes for, but unfortunately, didn’t love. The only memorable items were the cocktails and the honey butter cornbread. The portions were massive, which would normally be a plus, but overall, the food was just OK. This is one we’d skip on a return trip.
After dinner, we made our way to Second City for their late night show, “The Devil is in the Detours.” It was hilarious, smart and fast-paced - exactly what you’d want from a night of improv. The shows rotate, but we’d definitely recommend checking out this spot if you’re in town.
Day 4: Beach Views, Deep Dish and Goodbyes
On our final morning, we had breakfast at Venteux located on N. Michigan Ave. The cafe inside is beautiful and gives you that classic “brunch in the city” feeling. Jen had the Duck and Waffle, Greg had the Eggs Benedict, and we both agreed it was a great way to end the trip.
We spent our last few hours walking the Magnificent Mile one more time, then followed Lake Shore Drive down to Oak Street Beach. Yes - Chicago has a beach. It’s small, but surprisingly scenic with some awesome views of the skyline. As dog parents, we love how dog-friendly the city is. Jen had to stop herself more than once from asking, “Can I pet that dog?”
Before heading to the airport, we grabbed lunch at Lou Malnati’s to try the famous Chicago-style deep dish pizza. We’re glad we gave it a shot, but…it’s probably not our thing. It wasn’t bad, but it’s not something we feel the need to repeat.
We had an amazing time in Chicago - great food, unique experiences and just enough walking to feel like we earned all those meals. While we didn’t use points for every part of the trip, we still saved significantly thanks to our credit card strategy, especially with the hotel stay. If you’re curious how we piece together trips like this - using points when it makes sense and paying cash when the value isn’t there - we’d love to help you do the same. Book a consultation and we’ll worth with you to build a personalized strategy that helps you earn more points and travel better.