Catching Up With The Windy City

The last time I went to Chicago was to celebrate my 30th birthday. Yay! This very important milestone required four star treatment so my husband booked us a room at the famous Drake hotel (referenced in the original Tom Cruise Mission Impossible movie), and I got courtside seats (well row 8) to a Chicago Bulls vs. Phoenix Suns game. We stopped to eat at Gino’s, at Billy Goat’s, and at Piece Pizzeria. We took the architectural river cruise and drank a few pints at Goose Island Brewing. By the end of our trip we had had drinks in the Hancock Building’s bar, visited the Adler Planetarium and taken pictures of each other from the Willis Tower’s observation deck glass boxes.

Day 1:

Fast forward a few years into the future and here we are, again, on our way to The Windy City. It is the middle of spring but the weather forecast calls for 77+° F temperatures for the weekend. I think it is safe to say that we have scored. 😀 We are hoping that the wind chill factor doesn’t mess too much with the sunshine, and that the shaded areas of the city remain enjoyable.

Trivia: At the base of all those skyscrapers it can get chilly and the pressure differential makes doors hard to open and close. That’s why they invented the turnstiles or revolving doors, to counter the pressure and be able to access the lobby.

The opportunity to take this trip arose from my need to use my Delta SkyMiles Reserve complimentary companion ticket. Turns out that my best friend (see My Adventures as a First Time Matron of Honor) lives in the city and since we have never been together in an adventure abroad, meaning outside of our place of origin, it was a good excuse to meet up and spend some time together. As a local, she would have more insight as to what to do and when to do it, being able to skip all the tourist traps for an authentic experience. Instead of staying next to the Water Tower, we decided to stay on the other side of downtown which was coincidentally closer to where my BF lives. The Hampton Inn Downtown is close to Adler Planetarium and Soldier Field, and next to the famous Bean. (We had to skip it last time because it was raining throughout our stay.)

Tip: To get around the city, you can buy one and two day passes for the City and Double Decker tours which have stops throughout the downtown area at major attractions. Use the water taxis and river cruises to complement the journey. The architectural tour is one of my favorites and departs from the city Center near Trump Tower and the Navy Pier. Most bus stops have information kiosks and catalogs of offers which include these and the Gangster tours. 

The drive to the hotel was brutal! There was traffic everywhere, start and stop all the way to downtown.  Halfway through the taxi cab journey it started to rain which slowed us a bit more. Taking into account that the 80°F could be felt, we didn’t mind being stuck in an air conditioned car for an hour. We checked in with my friends and we ate dinner at Union Sushi and BBQ. Worth the price just to taste their black rice rolls.

Since we are into draft beer and spirits, we decided to track down a good bar and my BFF told us about The Drifter which is an original 1920s Speakeasy. After stumbling about The Green Door’s basement, we found the secret passage door and landed in the smallest yet coolest establishment we had ever seen: they had a nice wood bar, tables for up to 37 people and a stage. Imagine our surprise when the show, for which we paid a cover charge of $10, turned out to be a burlesque dance! The hula girl routine she pulled off was very tasteful and entertaining; the comedian that followed her was excellent too. The cocktails were unique and well executed. Best Manhattan I have had in years! For desert we went to Eataly and had some gelatos, then we toured the second floor to check out the beer, wine and charcuterie selections. After a short walk, we went back to the homebase to chill, had a few at the nearby Emerald Loop Irish Pub and went to bed.

Day 2:

The illegal street racing in the lower deck of the loop didn’t let us sleep very well so we had a rough start on Saturday morning. We met up with my BFF and her hubby and headed to the Market by Jewel Osco to get some picnic supplies. Armed with a picnic backpack that made us look like school children, we walked the city and the beach front settling on a spot in Lincoln Park to make our sandwiches and sit down for a nice meal. A little cute white dog tried to steal our meats but his efforts were thwarted by his owner. Hehe. The overcast weather held and eventually cleared making our walk a lot more enjoyable and giving us a chance to visit the free Lincoln Park Zoo and the Lincoln Park Conservatory (of plants). The variety of animals at the zoo, especially the gorillas, and the collection of palms, ferns, orchids and flora at the conservatory were varied and exquisite. Not bad for a “for donations” run pair of attractions. A must see if you are in the city.

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After a stop at Starbucks and a long walk back to downtown, we parted ways at Quartino’s around 4pm because our hosts had an engagement to attend and they recommended we try the Italian fare, one of the best in the city. It turns out that the restaurant served family style meals so we were able to mind my husband’s diet and order gnocchi and sea food to curb the calories. We paired the meal with duck prosciutto and a nice Vino Verdhe Rose. So far none of our meals has been inexpensive and for the $60 tab, we can say we were satisfied. The 10.5% tax is killing me!

Back at the hotel, we sat at the Chicago Motor Club Bar and had a few Revolution Brewing beers which I reviewed in the Untappd app. The bar tender explained how this up and coming brewery is doing great strides to promote themselves and become exclusive on tap providers for local joint such as the hotel bar. After trying their Cross of Gold and Fist City, we were very grateful for their efforts. Beer this good belongs in Seattle or Portland, not on a Midwestern mecca. Hehe. I hope it finds it way over to the PNW. It is delicious and very rich in flavor. Best pit stop ever! Plus our bartender Mike was really nice and knowledgeable in all things beer, making our stay at the bar even more enjoyable and meaningful. Brews and knowledge, FTW. (And then Golden State managed to Warrior their way into a Western Conference Finals Game 7.)

Day 3:

After a 20 minute fight with the air conditioning in our room to get it out of heater mode and into the cooling setting, we rushed through our morning routine to meet with my BFF and her hubby for brunch at the LYFE Kitchen. The place serves meals under 1000mgs of sodium and around 600 calories or less. Inspired by the lack of healthy fast food, an ex McDonald’s executive launched this venture with good results. The food was delicious for the low salt content and can be appreciated by those with dietary restrictions due to high blood pressure. A real life saver for my hubby who had been eating smaller portions to keep his sodium intake as low as possible in a place full of junk food and rich Italian fare. Afterwards we stopped at Peet’s Coffee for tea and headed to Millennium Park to check out Buckingham Fountain and the Art Institute’s gardens. A homeless man offered to escort us through the park when we got lost for a burger meal. My husband always gets some random stranger to ambush him during our vacations, and at least this time it was to pay it forward.

Back at the bar, we had a few beers at the hotel with Mike, the bartender, while my friends took care of some work requests (so they can spend Monday at the Cubs guilt free). Around 7 we ordered Giordano’s deep dish and gluten-free pizzas with a delivery time of an hour and a half! Apparently the Memorial Day weekend rush was in full swing. To kill the time, my BFF showed us her wedding albums while we drank beers and enjoyed some snacks. When the food finally arrived we were starving! The fare wasn’t bad but it wasn’t spectacular. Not worth the wait in my opinion but a must for those wanting the local experience. The gluten-free option was to die for though. From there we went off to bed to make sure we woke up early for the Cubs 1:20pm game.

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Day 4:

My BFF made us a home cooked meal (rice, garbanzo beans, roasted  chicken and salad) before going to Wrigley Field. Home cooked meals are definitely the best. Yum! While we were eating my husband checked the game time and it had moved to 4:05pm! Wow! ESPN picked it up so the time had to shift for national TV, hopefully the Cubs will beat the Dodgers. He he. Now what to do to fill in the afternoon… Aha! Since I had forgotten my Cubs gear at home, we went shopping at TJ Maxx and Marshalls to get a remedial shirt. We lucked out on our first stop and we were able to head back to the train to depart for Wrigley Field. My friend had won the tickets as part of her employee perks, but I hadn’t known until today because her text never made it to my inbox! Row 7, Section 133, in the second oldest MLB stadium, here we come!

Tip: Take the train at least an hour before game time or you will risk being late. The train fills with regular passengers as well as sports fans and they track occupancy to make sure the compartments aren’t strained. Some people take Uber or rideshares but the park access is limited so you will have to wait in traffic and walk a few blocks to get there. Keep this in mind especially during peak hours and seasons.

At the risk of sounding spoiled, the 80 degree sunshine was killing us so we had to abandon our seats and moved inside the concourse to avoid getting heatstroke. The SPF 30 was doing its job and we didn’t look like we had been roasted (most guests did). While we took shelter, the Cubs scored 2 runs! One right after we had finished waiting in line for the bathrooms and the other while we were in line to get water. If it wasn’t for the picture we took with the Cubs’ mascot, all would have been for naught. He he. We sat down and watched the game through the 7th inning and left before traffic got heavy. The train had seating room available and took us swiftly back to downtown.

Because OKC and GSW were playing, we said our quick goodbyes and ran back to the hotel to spot ourselves in front of the lobby bar’s TV. The guest relations specialist and our bartender found us an Italian restaurant called Belle Bacinos that delivered the best filet Gorgonzola and seafood fare we had tried in a while. (The restaurant is on the same street as the Hampton Inn.) Between the beer and free drink samples we were served, the game flew by in a haze of excitement and in good company. It was sad to see Durant and OKC go home but as a Sonics fan, I applaud karma for avenging us. (No hard feelings…)

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Up in our room, we packed, fell asleep and woke up the next morning with a mild hangover and a lot of acid reflux. A small price to pay to have had so much fun in the city. It felt like a vacation done right. Day 5 is filled with plane, trains and automobiles; nothing extraordinary to report. Hopefully our trip is uneventful. If it isn’t, expect an update below.

Many safe and happy landings to y’all!

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