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How to Enjoy Chicago Post-Pandemic (July 2021)

What's not to love?

We love Chicago, so it’s no wonder that we decided to take our first BIG post-pandemic trip to a place that we already know and love. (–We JUST came back from Nashville ( , but there were so many surprises about the town that we were disquieted by ( , that we knew we wanted to go somewhere that we thought would be soothingly familiar. –We also could NOT travel to our other favorite place, Toronto, due to international travel restrictions STILL being in place.

We decided that instead of putting our memories in a photo album, we should share our experiences this time with anyone interested in what travel is like nearly post-pandemic (July 2021). What follows are some notes about our trip.


I n i t i a l I m p r e s s i o n s :


Restaurant Concessions

Restaurants have had to make concessions due to the pandemic, but many seem to be finding their own way. We can’t even really imagine what the dining choices would have been like if there HADN'T been a pandemic. We are new to trying to find unique restaurants and to finding local fare, so there seemed to be an OVERWHELMING array of choices, depending on what we were in the mood and had the budget for. 🌮🥩🍩😎🍸👏🏾


Weather did NOT cooperate

It was REALLY hot during these days, so we tried to NOT take walks longer than 10 to 20 minutes at a time. Our goal was to NOT burn ourselves out—literally—and to stay hydrated, so that we would stay motivated to continue on and be in the mood to try more and if trying new things.


Refreshing us pit stops

We’ve been using Starbucks along the way as places to stop, refresh, and to reboot before we head to our next adventure. @starbucks


Taking the city bus/train

Better than walking a minute longer in the hot sun. It saved our day, to be honest. We took the train back. The 7 day, all access pass covers the train AND bus for $30. The Uber rates have been crazy, so we haven’t used them at all. 😳🙌🏾


Random Art

Similar to our Nashville experience (add link), we found so much beautiful and clever street art that we just had to share some of it with you.


Other randomness

As always, there are photos that don’t believe anywhere else, but seemed fun enough to be included.


Residence Inn/Marriott (Downtown/River North)

The location is good. Room is worn. The lamp was broken when we arrived; reported it and it was fixed within a couple of hours. Security is pretty good considering the location. LOVE The Body Shop products given complimentary in the room. No maid service due to pandemic protocol. Finally got used to that, but it was nice to be informed about this early on —unlike our Nashville experience. 🤷🏽‍♀️


I n d i v i d u a l E x p e r i e n c e s :


See It All Mini Bus Tour

Host was funny, personable, and informative. Allowed us chances to get out at a few stops to explore and take glamour shots. Didn’t like that we had to wear masks, but did so anyway….🤷🏽‍♀️


Chicago Riverwalk @chiriverwalk

Chicago Riverwalk (Re-launched in 2015; restaurants, gelato, bars, boating docks and plenty of spots to sit and admire the views); floating gardens between Wells and Franklin Streets. Took a stroll after one of our romantic dinners just to take in the views.


Grant Park Music Festival

Classical music; runs through August 2021; Didn’t formally get tickets to the concert, but explored the area; enjoyed the flora and fauna of the botanical garden before heading back toward the hotel. 🪴


Time Out Market Chicago @timeoutmarketchicago

18 restaurants in one place; 916 W Fulton Market Chicago 60607; We ate beef brisket from a place called Soul & Smoke. Great branding. Tasty. But there were no sides—like friends or Mac and cheese—so we felt just a little more in-satisfied than we might’ve for a normal restaurant. 🤷🏽‍♀️ The bus-staff at the facility are superb, however, and make an effort to actively wipe down surfaces once eat party is finished.


Siena Taverna @sienatavern

Trying to finish off dinner; ended up at this place we’d passed a few times across from our hotel. Was pleasantly surprised that it was “real” gourmet food. Everything was tasty and being on the open air sidewalk patio WASN’T as annoying as I had originally thought it would be.


JoJo’s Shake @jojosshakebar

Since Day One, we KNEW we had to get our hands in one of these fun and festive shakes with all the trimmings. Wasn’t disappointed. In fact, liked how the staff made sense out of some line confusion that was erupting and took care of waiting customers by sending a staffer out to the curb to take orders. Thumbs waaaay up for these guys! 🥛


The Little Goat Diner @littlegoatdiner

Wait wasn’t long —especially since we didn’t have reservations. Ambiance was hipster-cool and waitress was chatty, which I think is their vibe. The dish we had planned to try—upon a recommendation from a friend—has been taken off the menu due to the pandemic, but what I ordered wasn’t bad, but the kick-ass component of this meal was the biscuit—which tasted like half-donut/half-biscuit and was flaky on the outside, but tender on the inside. Perfect! If I had known about THESE, I WOULDN'T have wasted calories on the “main course”! 😳🙄


Harry Caray’s Italian Steakhouse 🥩 @harrycarays

We ducked into this place, looking for a burger and fries and realized that they are a hifalutin romantic as all get out spot. We booked a reservation for the next day and that’s where we’re having our once a vacation romantic dinner. So far, I am having a different and indulgent Key Lime Martini. 🍸

They play Frank Sinatra songs and keep the lights low. Just what we like for our first romantic dinner out.


Portillo’s Chocolate Cake Shake @portilloshotdogs

Found a recommendation for the chocolate cake shake on YouTube, so we went there to try it (since it was right down the street from the hotel). The restaurant was chaotic—as was the online ordering process. We FINALLY got our shake. Was NOT as tasty as we had been led to believe. –Actually, our Starbucks Funnel Cake Frappuccino is a tastier, healthier alternative to this 1,400 calorie desert. –But….. at least we checked it off our Chicago “To Try” list. @starbucks


Stan’s Doughnuts 🍩 @stansdonutschicago

This was another of those YouTube travel video-recommended delicacies. Great branding; loved the bag and the retro dining room. Luckily, we ran right into it after walk about the universe, so we tried it. Perhaps they needed to be super fresh to be tasty, but we were disappointed.


“The Obama Portraits” Art Institute of Chicago @artinstitutechi

Appreciated having the opportunity to not only attend the Art Institute of Chicago for the first time, but to enjoy “The Obama Portraits” exhibit WITHIN the entry ticket price! Had to be let in for appointment slots to see the portraits—which was probably necessary, although annoying!—but it was nice to punctuate our visit to Chicago by seeing the history of its most successful residents.


Guitar Center (Halstead Ave)

Same low-energy customer service that we’ve grown to dislike—no matter what state we’re in. And when I say “low-energy,” I mean “no energy.” We we’re there about 45 minutes, played about 5 different instruments, in 4 different rooms, and not ONE employee greeted us, nor asked us ANYTHING. —That’s on top of the fact that, although there was a person stationed at the door, he did not say not one mumbling word to us. If we HAD wanted to buy something, we were discouraged to do so by folks who seemed as if they didn’t want to serve us. Same store culture; different store.

Chicago Music Exchange @chicagomusicexchange

Appreciated that CME is not making EVERYONE wear masks; only those who are unvaccinated. Also, appreciated that customers are freely allowed to play the premium basses—which seems to be rare with SOME music stores. Not only that, but we were greeted warmly at the door and felt welcomed to explore, but also to ask questions, if necessary. (As you will recall, this is our second trip to CME, here is our first: )


Chinatown Neighborhood

It was nice to see it up close, but I felt more like an interloper instead of like a welcomed visitor. But I kinda understood why, because as we walked down the main thoroughfare, we noticed the aftermath of some smashed in—and then boarded up—windows. The people there are probably not sure if we’re there for good or for evil. Add to that that it was early, shops were barely open, the entrances are small, crowded. Only the first few larger shops seemed situated for browsing, so I decided NOT to make this a shopping trip. Instead, we spent MOST of our time at Tom Ping Memorial Park, which was well-worth the search. It is a beautiful, natural, peaceful oasis on the river’s edge, where you can see the downtown cityscape from SUCH a beautiful perspective. —It was such a shame that the Chicago Water Taxis are out of service—due to coronavirus—because we would have landed at this park first. On the other hand, because the park is SO out of the way and obscure, we got a chance to take it all in quietly and without many people around, which had a calming effect on us.


Greektown Neighborhood

Similar to Detroit’s Greektown “neighborhood,” it was less than spectacular. In fact, other than the monuments at the beginning and end of the area, it is roughly the same—small—size as our own Greektown. Bruce points out that there may be a few more ACTUAL Greek-themed businesses in the Chicago version. I was happy that we literally wandered into the area after visiting the WNDR Museum. If we had made a SPECIAL trip there—on this INCREDIBLY hot day—I would have been extremely upset.


Lou Malnetti’s Pizza @loumalnatis

We decided NOT to make a mission out of comparing Chicago-style pizza—like we did the very FIRST time we came—but we had seen another YouTube travel video that recommended this pizza over ALL the others, so since we hadn’t had any of this variety, we decided to make it a MUST on this trip.

While I don’t remember which pizzeria won our stomachs last time, I can just say that our own Greektown favorite deep dish-style pizza—at Pizza Papalis—STILL wins over even this one. The crust was much too thin and not as tasty as our Detroit version. It was nice to check it off our culinary list, though….


Beatrix Café @beatrixrestaurants

We were so hungry one evening and did not want to try any ONE restaurant more than once, so we stopped in yet another place right down the street from the hotel. We ordered burgers and I don’t know WHY I expected a whole wheat bun, but I ended up with whole wheat bread…. We were grateful that they were still open at this late hour and that, even though there were no tables available, that they provided a takeout menu. Took our food back to our room, ate, and crashed.


Starbucks Reserve Roastery @starbucks

This is the largest Starbucks restaurant in the United States. Line was ALWAYS queued around the block, so we never were convinced to wait in the 90 degree heat to browse the 4 floors of roastery, restaurant, gift shop, and apparel store. Maybe next time….


Baseball Game @cubs

First time ever at Wrigley Field (for Cubs v Phillies game). Yet another item that we got to check off the list that we had NEVER done in Chicago before. –No, THAT guy is NOT with us, but he is DEFINITELY the center of attention….🙄 #chicago #wrigleyfield #cubs #baseball #prejippie #bloomingprejippie #travel2021


The Brown Elephant Thrift Store @howardbrownhealth

We found a way to hit two places at once. While thrifting wasn’t our primary activity, when it was JUST 10 minutes—and on the same street—from something that we had already planned to do, it was a no-brainer! Even better, all proceeds from our thrift purchase benefits LGBTQ health and fund care for the uninsured and under-insured at Howard Brown Health. Found two cool tops AND donated to charity ON OUR WAY to the Grand Finale for the day. Yay!


Cruz Blanca 🌮 @cruzblancachi

Have been FIENDING for fried fish tacos and this place looked promising. ‘Turns out that the covid modification of their menu meant that the only similar option for today is fried shrimp tacos. ‘Turns out that they were THE bomb! 💣 This meant that I could check this off my list, while sampling a cool little spot in the Fulton Market District—which, by the way, is RIGHT down the street from both Time Out Market Chicago AND The Little Goat Diner (noted above). This area is chock full of quaint, but fresh, prepared from scratch food restaurants. Yum. 😋


Firecakes Craft Donuts 🍩 @firecakes

Needless to say, we kept seeing these lovely branded boxes and Bruce couldn’t HELP but ask folks where they were. We realized that it was right around the corner from the hotel, so we headed there a couple of times. It took a couple of times to be able to get it……. The place is about 10 square feet, which meant that they weren’t letting more than one party—no more than 5 people at a time—in the space to choose donuts. Cute little place with donut ice cream sandwiches—which it was TOO hot to take advantage of!—so we got 5 donuts, which meant that we did NOT get the cool box! 😔 But we got TOTALLY desperate for an original dessert one evening, bought half a dozen, and got the box! Yay! 🍩 Donuts weren’t great, but they beat Stan’s, in our opinion, and gave us that chocolatey sweet item that we needed before bed. 🤷🏾‍♀️


Rock Bottom Café @rockbottombrewery

It was one of those late evenings again and we went in search of a new place to try. This one was finally open and not already at capacity—as it had been the two times we’d tried to stop there before—so we tried it. The food was tasty enough, but “chicken and waffles” meant “chicken strips and warmed up waffles,” so it was NOT the gourmet experience we had grown to expect from the restaurants around here. Better than going to be hungry, though, and the staff was very friendly.


WNDR Museum @wndrmuseum

This operation has done quite the job on promotion, as I read—more than once!—about it before we left Michigan. It was billed as “interesting visual/audio installations.” Wasn’t happy that we had to wait out on the sidewalk—in the hot sun—when we had appointment slots that we were right on time for. We thought it was going to be the “poor man’s immersive Van Gogh” experience, but it turns out it was more like a collection of selfie stations. Our daughter might have been more poised to get the most out of it, but once we saw what we were in for, we TRIED to lean in….. but that was hard, because we were wearing masks, so selfies were NOT an option for me. I applaud their efforts—and probably would have come anyway—but knowing that there were going to be NO selfies taken made me resent not knowing what to expect…. –This would have been a SUPERB space to shoot our next music video in, but we would need to be able to take a take in EACH room.


Smith & Wollensky Steak House 🥩 @smithwollensky

We had our final, most romantic dinner on the Chicago riverfront. The online reservations didn’t work, but when I called, we got booked that same night. And a window seat too. It was a Wednesday, so that probably wasn’t as hard as it COULD have been. The food was tasty and plentiful, and the service was friendly. –And did I MENTION that we had a river view? Quite a lovely evening for our last night in town.

Well, that about does it. This wraps up our most recent trip to one of our favorite cities, Chicago, Illinois.

What city are you ready to go back to?

Or where should we travel to next?

We’d LOVE to hear from you! Drop it in the comments below.

If you’re interested in more of our travel adventures, check out this playlist of travel-related vlogs:

As always, wishing you Peace + Joy!


More Ways to consume B L O O M I N G P R E J I P P I E :

· All things “Sugar Fit”:

· Gab & Jam podcast:

· Soundcloud (music):

· Funky Happy People (Who Listen to a Variety of Genres of Music) Facebook Group:

· Be the Next D.I.Y. Rock Star Facebook Group:



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