one of the best parts about traveling is getting to share your stories/recommendations with everyone when you return. so after spending five days in the windy city, S and i are excited to share our must-dos, must-sees, and must-eats. if you’re planning a trip to chicago or thinking about visiting in the future, i hope you can use our experiences as a resource guide for reference as you prepare for your getaway! be forewarned, this is a long post 🙂
first and foremost, before visiting any new locale, i always do my research. our trip to chi-town was no different. i used an amazing summer city guide found on chicago-based blog, sequins & stripes, and catered our agenda around S and my personal tastes and interests. having just visited the city two years ago, S had a lot of experience and knowledge of his own which was also super helpful in planning our day to day activities. it was in our initial research that we also learned that the nfl draft was going to be in town during our stay. while the weather thwarted any real exploration of the facilities, the event definitely brought an added electricity to the city.
accommodation planning began months before. we opted for non-stop flights on southwest into midway which proved to be incredibly convenient -only about a thirty minute cab ride into the heart of downtown. after extensive research on orbitz, S and i settled on a hampton inn off michigan avenue (one of the main streets in the city) for our hotel. it not only proved to be fairly central to everything we wanted to see, but more importantly, had great customer reviews and offered competitive per night pricing. the best thing about booking with a company like orbitz is that your trip is nearly paid for by the time you arrive! all you have to worry about is excursions and restaurants during your stay.
with 6:20 a.m. flights out of san diego on wednesday morning, we landed at a hair past noon (with the two-hour time difference), with half of the day still at our disposal. we checked into our hotel, set down our luggage, and immediately set out for something to eat. we headed to goddess and the baker, a restaurant that i had earmarked for its plethora of “shawna-style” (see also: vegetarian, vegan, and gluten-free friendly) offerings. in addition to sandwiches, salads, and baked goods, they also had an extensive list of specialty coffees and teas.
with food in our bellies, we set out to explore. since san diego is so spread out, it’s always nice visiting a metropolitan city like chicago where everything is within walking distance. first stop was millenium park, home to the iconic (and instagram famous) cloud gate sculpture better known to you and i as “the bean.” the park boasts tree-lined walkways and opens to an outdoor amphitheater where everything from group yoga to music festivals are held.
from millenium park we headed down to the waterfront. having grown up a few miles from the pacific ocean, it was hard to wrap my mind around the fact that the blue water (it was seriously so clear!) that was lapping along lake shore drive was not from the ocean, but from a lake! lake michigan, to be exact. they don’t call it the windy city for nothing as the breeze was definitely stronger by the water. with the forecasted showers at bay for now, we followed lake shore drive all the way down to navy pier. similar to coney island or santa monica pier, navy pier boasts restaurants and attractions, including a giant ferris wheel.
we wound our way back from the waterfront into the heart of the city. in realizing how far we had walked (we guessed around 5+ miles), we agreed celebratory chicago deep-dish pizza was in order (well for S, at least). so we walked over to giordano’s -one of the city’s famous purveyors of fine italian cuisine and took our order to go so we could enjoy our hard-earned meal in the comfort of our hotel room. S was in deep-dish heaven while i dug into one of the better chopped salads i’ve had in a while.
with showers forecasted a majority of the day, we elected thursday to be our “inside activities” day. ironically other than intermittent sprinkles, the day turned out to be clear, albeit very cloudy and cold. we began our day with a short walk to kanela breakfast club, another pre-screened eateries and by far my favorite restaurant of our trip. if you like mason jars, an eclectic menu, and friendly staff, kanela is definitely worth a visit. we admired the the charming decor as we sipped our coffee from camping mugs and planned our day. though everything looked tempting, we finally settled on the steel cut oatmeal with coconut shavings, blueberries, and granola, and the baked french toast. i’ll let you guess who ordered what 😉
a screenshot from snapchat, are you following along yet? come find me at iamshawnaleeann
after breakfast we set out to start our day of arts and culture. of the many museums and attractions the windy city boasts, we set our sights on two in particular –the field museum and the art institute of chicago. for the traveler on a budget, museum visits can really add up. that’s why we were happy to know about the city’s “go chicago” card which offers patrons access to up to five different pre-selected attractions of their choosing for a flat fee. S and i agreed upon the pass with admission to three attractions and from the list chose to visit the field museum, the art institute, and the city’s famed architecture boat tour (which we reserved for the following day).
having grown up with the occasional field trip to balboa park in san diego, the field museum of natural history was very reminiscent of museums i had visited in my youth. which is appropriate seeing as on our particular visit, the museum was crawling with tiny humans enjoying a similar scholastic experience. aside from rooms of artifacts from an array of cultures and time periods, the field museum is home to sue, the largest, best-preserved, most complete t-rex ever found.
after our tour through the museum, we ventured over to soldier field, home of the chicago bears. though i haven’t been to many nfl stadiums, i have to believe the iconic venue is among the most picturesque. if t-rexes and football don’t interest you, also located nearby is the shedd aquarium. if underwater life is more your speed, the aquarium is also among the listed attractions on the “go chicago” card.
from the field museum, we walked back down michigan avenue to the art institute of chicago, named “best museum in the country” by trip advisor. it’s easy to see why the institute earned the coveted title as room after room featured work from some of the world’s most iconic artists -everyone from vincent van gogh (whose work was showcased in a special exhibit) to andy warhol.
we finished off the day with a little pre-dinner shopping followed by a meal at tortoise club. though our original dinner plans had included a visit to public house -a casual gastropub and sports bar boasting my favorite side dish -roasted brussels sprouts (duh), the fact that it was thursday night (a popular night, i’m told, for going out for a drink with friends) and not only that, but the first night of the nfl draft, increased the typical wait time for a table from 10-15 minutes to an hour at best. so it was by happy happenstance we landed up on tortoise club, but aside from feeling very under-dressed upon entering past its double doors, our drinks (i had one of the best, if not the best glasses of moscatos i’ve ever had), our meal, and definitely the service far exceeded any initial expectations. the restaurant has a supper club vibe with its dim lighting and softly playing music as background noise. if you’re looking for a proper date night in the city, i highly recommend. but heed our advice and maybe leave the knit beanies at home (whoopsies).
we tempted our good weather streak for a third day with a friday full of outdoor excursions. first up was the architecture tour along the chicago river (the third of our three allotted passes on our “go chicago” card). if there’s one thing i heard most from people learning of S and my upcoming travels, it was about this tour. “it’s a must do!” they’d say. and now having experienced it, i can echo the group sentiment. whether you’re interested in architecture or not, the tour is a fun and engaging way to learn about chicago and its rich history. our congenial tour guide jim also helped ensure our 75-minute tour was entertaining. his witty quips were almost enough for me to forget about the loss of feeling i was experiencing in my lower extremities as i had carelessly misinterpreted the forecast of “clear skies” to mean “break out your sunscreen, it’s bathing suit weather.” yeah, no. there is cold and then there is cold. as i said in a previous post, midwestern “cold” is bitter, bone-chilling, and quite humbling for a born and bred californian. i all but ran to the hotel room after docking to exchange my lace-up flats for two pairs of socks and my rain boots.
we continued our friday fun with a trip to the iconic wrigley field for an afternoon game. regardless of your feelings toward america’s favorite pastime, i think many would agree the infamous baseball park deserves a spot on any bucket list. it was certainly on mine! S purchased tickets from his phone (isn’t technology grand?) for the 1:20 p.m. game pinning the chicago cubs against the atlanta braves. to ensure we got the full chicago experience, we even took the L-train to the game. having experienced the wonder that is public transportation during my time studying abroad in spain, i felt a little nostalgic as we boarded the crowded cars, joining fellow game-goers dressed in the the cubs’ signature cobalt blue.
the ballpark was abuzz with fans, happy to be getting an early start to their weekend. the smell of sauteed onions and draft beer filled the air. we filed into the ballpark and found our seats at terrace level, stopping first by a kiosk so S could get his long-anticipated chicago dog (complete with neon green relish, mustard, and sweet peppers). though we had strategically chosen seats beneath the overhang of the deck above in case a fortuitous rain shower had decided to rain on our parade (literally), we soon learned that despite it offering shelter from an inpromptu storm, it also acted as a mini wind tunnel, only exasperating the chill that was creeping its way past my three layers of clothing. don’t judge me when i say this, but we lasted three innings. i’m half ashamed to admit that out loud, considering how special an outing at wrigley would be for many of my friends and family, but when you start to lose feeling in your fingers and can’t quite get your teeth to stop chattering, you reevaluate your situation very quickly. thank goodness S felt the same way. we took the L back into town and promptly sought refuge in our hotel room for the next two hours, only emerging again to grab a bite to eat at roti mediterranean grill -a google find offering fast-casual greek cuisine. the evening ended the same way it normally ends on a friday night -by flipping between old episodes of say yes to the dress and diners, drive-ins, and dives.
saturday greeted us with the weather we had feared since our arrival -a cold, windy, rainy mess. the power of starbuck’s clearly knows no bounds because somewhere around 9:30 a.m., we decided to brave the elements (i’m being a tad bit hyperbolic, admittedly), for americanos and acai bowls from the protein bar. we mulled around the hotel room for a few more hours, unsure of how to spend the final hours of our chicago vacation. surely we couldn’t let the time run out cooped up in a hampton inn (no offense hampton inn, you really were quite lovely)! so back to the list of pre-screened activities we went, an email i kept at the ready in my phone. pleasantly surprised by how many items we had already checked off during the duration of our stay thus far, we finally concluded that a trip to the lincoln park conservatory would be a great (and enclosed) way to spend the afternoon. if the weather had been more ideal, we probably would have stretched our legs with a hearty walk to the site, but since it was still quite dreary, we opted for a cab instead. now i have a more extensive post about our time at the conservatory scheduled for friday, so i’ll refrain from too much detail here. but let’s just say it was the perfect anecdote for our rain-induced cabin fever. and the best part was, it was FREE!
for our final meal in the windy city, we opted for sunda, an asian-fusion, sushi house known for its creative small plates and cocktails. given my love affair with brussels sprouts, it should come as no surprise that we ordered the crispy brussels sprouts salad (made with red cabbage, fried shallots, and minced shrimp vinaigrette. according to our server (and most of the restaurant’s yelp reviews), the dish is a must-try no matter your pre-conceived opinions about the humble sprout. i shared our portion begrudgingly). though the plates are designed to be shared, S and i ordered our own entrees, he opting for crispy rice with spicy tuna and lemongrass beef lollipops and i, the pad thai with tofu. everything was delicious and left us pleasantly full (did i mention we also began our meal with two of their delicious cocktails? i highly recommend the “lady and the champs” made with aperol, st. germain, blood orange liqueur, moët & chandon, lemon juice, and grapefruit bitters). which really just translated to “please bring us dessert.” when i had made the reservation that afternoon, the voice on the other side of the line had inquired if we were celebrating anything that evening. “our engagement!” i happily replied. and what a perfect way to commemorate our first official week as fiances than with a slice of complimentary chocolate cake and champagne?! buzzed (at least i was) and happy we piled back into a cab en route to our hotel to pack up and prepare for our early morning departure. the next morning we boarded our mid-morning non-stop flight back to america’s finest where the warm southern california sun we know and love (and will never take for granted again) was waiting for us. and just like that, our vacation had come to an end.
bitterly cold weather aside, chicago is truly a wonderful city full of things to do, see, and eat. if you’re thinking about planning a trip, i highly recommend you go! just make sure to bring a jacket, your walking shoes, and a craving for deep dish pizza.10