Chicago 2.0

Chicago2014We were able to head back to Chicago for Independence Day and my 30th birthday (yikes!) thanks to an aptly timed professional development conference for work. My boss has been wonderful about letting us add on a few days when we attend conferences to enjoy the destination, and I usually also take my husband along since he can easily work from our hotel room.

It was really hard to believe we hadn’t been to Chicago since 2010, and that was also during Independence Day weekend. Since this was our second trip, we decided to focus on a few things farther away from the city center that we weren’t able to do before, and we collected tons of recommendations for places to eat and booked a bunch in advance to help build out our itinerary.

We stayed at the Sheraton downtown as part of the conference portion of our trip, which was very nice. But even better was the Hyatt across the river where we stayed during our personal time, which I was able to get for $80/night on priceline! Only having to pay for one flight, a few $80 nights at a hotel and some of our food made the trip acceptable to my husband, who enjoyed reminding me we just got back from Morocco, Spain and Portugal a couple of months ago.

The weather was beautiful the first few days– bright blue skies and warm– but it got overcast, rainy and hot for a few days in the middle before straightening out for our departure. It didn’t bother us at all aside from making some of our photos a little boring with gray skies and clouds.

We visited SO many restaurants that this post will focus more on our foodie adventures than anything. We love trying everything and anything and even a couple appetizers and a house cocktail can give you the flavor of a place. Here’s a whirlwind recap of our adventures in Chicago.

We landed mid-morning so we caught a taxi to the Hyatt and then strolled down Magnificent Mile, bought some Garrett’s popcorn, had lunch at the Slurping Turtle, and then took a seat in the beer garden on Navy Pier to enjoy the Marine Corp. band’s jazz set throughout the afternoon.
We headed to the Untitled for dinner and although I was overcome by exhaustion and unable to do justice to the apps we ordered, we both really enjoyed the atmosphere of this Prohibition-style eatery and the band performing was INCREDIBLE. I would love to go back for one of the late-night burlesque shows. We walked by another day before they opened, and since there’s no signage–in line with the Prohibition theme–we nearly missed it!
We started the morning at Glazed & Infused, an amazing little doughnut shop, which set my husband in good spirits! We then headed south of town to the Museum of Science and Industry, which we missed on our last trip. We were there for hours and really enjoyed the special exhibits on Disney and the U-505 Submarine. We also watched a D-Day film that certainly put me in the right mindset given it was July 4. We grabbed a sundae to share from the old-fashioned shoppe inside to tide us over until we could catch a bus back to downtown around 3 p.m.
We walked across downtown to Al’s, featured on Diners, Drive-ins and Dives, to share an Italian Beef, and then we popped across the street to Portillo’s to get a Chicago dog and drink. Unfortunately I left my husband in charge of drinks while I got food, so we ended up with goblets! We stayed and just watched all the activity until we headed back to the hotel for a nap.


We napped until after dinner time since we had a late lunch and then headed out to get some standing room for the late-night fireworks. We viewed them from Navy Pier last time and it was so congested. This time we stayed on the bridge by the river and it was much better–still tons of people, but you had a little breathing room. Afterward we walked across town to one of our favorite spots, the Redhead Piano Bar, for a drink and took a few late-night pictures before during in. On our walk back to our hotel we stopped at Uno Pizzaria for a late-nigh snack, but people were being crazy with fireworks outside so we just got our pizza to go and had a slice in the hotel before calling it a night. It was a great Independence Day!
We slept in the next morning and then started our day–which was quite overcast–with a walk down to the river where we took a bridge tour and learned about the history of the river and how it impacted the development of the city. From there we walked to Millennium Park to get our obligatory photo with the bean, and then we wandered through some parks back toward our hotel where we had some leftover pizza for lunch.
After our afternoon siesta, we took the L up to Wicker Park to explore the neighborhood and the restaurant recommendations of some of our friends. We started at The Bedford, which is an old bank-turned restaurant. It was amazing–we have to go back. You can sit inside the old vault, and the walls are lined with old safety deposit boxes. Afterward we walked down the street to Fatpour Chicago where we tried the apricot cidre and Not Your Father’s Rootbeer, which is an incredibly dangerous drink as it tastes just like rootbeer! We ended at Bangers & Lace for something a little more substantial just as the rain set in, and we were able to get back downtown before getting too wet. We decided to have a nightcap at the BIG Bar in our hotel, and my husband rediscovered his new favorite appertif, the Negroni.
We slept in the next morning and then wandered to GT Fish and Oyster for my birthday brunch! We sat out on the patio, relaxed and had the most amazing food. It was a perfect start to our morning.
We walked back to the river and took a boat cruise of the river and lake. We had great seats up front in the shade so we continued to relax, take pictures and enjoy our morning. We walked across town to have lunch in a little district I wanted to explore, but everything was closed. We ended up eating some strawberry pie at the Little Goat and then taking the metro back downtown for an afternoon siesta.
We walked back to Navy Pier in the late afternoon to listen to the band for a while, and then we had dinner at the Purple Pig, which was wonderful! I love their slogan– Cheese, Swine and Wine. We had a pretty sunset and just wandered around at night taking pictures. It was a perfect 30th birthday for me!
Our last couple days we both at to work so we only had time to sneak out of our new hotel for a couple of meals. We tried another DDD recommendation, Big & Little’s, for lunch, and then we had some appetizers at the Public House for dinner and some drinks at Three Dots and a Dash, which was really fun. I ended up buying my husband’s drink glass as a memento–I’m hoping to place a succulent in it!
We went back to Wicker Park for our last night out and had the most amazing evening. We started at the Violet Hour for cocktails (my husband is standing next to the hidden doorway!), went to the Trenchermen for drinks and appetizers and then randomly popped in a little place called the Chop Shop and 1st Ward because they had a sign outside that said $1 raw oysters. We ended up eating two or three dozen and then walking it off as we made our way to our last destination, The Frontier. We had so much fun and it was the perfect ending to our amazing trip.

Foodie Insights: 

Slurping Turtle– Pork Belly Bao (delicious), Spicy Tan Tan Men Ramen (very good), Red Miso Ramen (very good)

The Untitled–Drunk Devil’s on Horseback (not the best we’ve had), Beef Cheeks & Scallops (excellent), House Pretzels (ok)

Glazed & Infused– Blueberry-Lemon Glazed (very good), Maple Bacon Longjohn (very good, but not the best we’ve had)

Al’s– Italian Beef (very good)

Portillo’s– Chicago Dog (very good)

Uno Pizzaria– Numero Uno Deep-Dish Pizza (excellent)

The Bedford– Roasted Mushroom and Gruyère on Toast (excellent), Gin Marinated Olives (excellent)

Fatpour Chicago– Chicken n’ Waffle Bites (delicious)

Bangers and Lace– Hot Links (delicious), House Pretzel (ok),

GT Fish and Oyster– Biscuits and Lobster Gravy (delicious), Crab Benedict (delicious)

Little Goat– Strawberry Pie (good)

The Purple Pig– Charred Cauliflower, Toasted Breadcrumbs, Cornichons & Parsley (very good), Meat/Cheese Board (delicious), Goat Cheese and Honey Schmear (delicious)

Big & Little’s– Soft Shell Crab Taco (very good), Big & Little’s Taco (very good)

The Public House– Bacon Mac & Cheese (good), Brisket Sliders (good)

Niu–Aloha Albacore roll (good),

XOCO–Fully Dressed Guacamole (good), Baja Chicken Sandwich (delicious)

Downtown Dog–Downtown Dog (good)

The Trenchermen– Pickle Tots (amazing)

The Frontier– Duck Tacos (ok)

One thought on “Chicago 2.0

  1. Pingback: Local Adventures: Worldy Fare | Heather's Compass

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