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The Best of the Windy City

I’ve been quite delayed in posting due to craziness involving wedding planning and work, but wanted to sneak in a great itinerary to the Windy City based on Max’s surprise 30th birthday trip there in May!

I had been to Chicago twice before, once when I was younger and another time in high school when I got to experience the Windy City at it’s windiest. Going to back to a city as an adult is always a new experience in and of itself, so I was excited to see it through a different lens. Max was a first time visitor and was excited to travel to one of the top places on his bucket list.

Looking to get the most out of your trip to Chicago? Here are some recommendations to get you started:

Stay in a convenient location.  

Coming from small-city Boston, I often forget how widespread other cities are! In researching locations in Chicago, every hotel seemed far from everything we wanted to do, but choosing a hotel in the River North / Magnificent Mile area is a great choice for visitors. Not only does it provide you with great views, but it also allows for easy access to some of the best things to do. We could not have been happier with our stay at the Westin River North and would return again. The location was great, the rooms were clean and spacious, and the breakfast was delicious!

river north

Take part in the beer scene.

Chicago is one of the homes of craft beer for a reason – there are a multitude of options and new breweries keep opening. The birthday boy was allowed to pick this part of the trip and opted for a trip to the Goose Island Brewery to try one of his favorite beers directly from the tap. There are two locations, but we visited the Clybourn location and had a great lunch in the brewpub after.

goose island

Cheer for the local team.

It is hard not to root for the Chicago Cubs! They have not won the World Series since 1917 and as Boston fans, we know the feeling of waiting a long time for that title. After Fenway Park, Wrigley Field is the oldest ballpark in baseball and steeped in a lot of history. The rain cleared just in time for us to take our seats in the right field grandstand (thank goodness!). It was a beautiful day for baseball and a big bucket list item for both me and Max.


Arrive with an empty stomach.

Contrary to popular belief, the Chicago food scene is not just about deep dish pizza and hot dogs. There were so many great choices, which made it was hard to narrow down just where we wanted to eat, but if you plan in advance you cannot go wrong. Stephanie Izard’s famed Girl and the Goat restaurant did not disappoint with innovative small plates that allowed us to try a wide range of food. The open kitchen makes the restaurant feel very welcoming despite the fact that is always packed. Ruxbin was our choice for our other dinner and was equally as delicious! This BYOB restaurant in Noble Square seats less than 40 people and makes the dining experience feel more like an intimate dinner party. Many of the tables around us were locals who visit Ruxbin often and were kind enough to lend their suggestions for dinner (which were spot on). Mexican food was high on Max’s list for the weekend and luckily our hotel was walking distance from Rick Bayless’ Frontera Grill. I thought it was a little overkill when people suggested making reservations for lunch (so I didn’t), but they were not lying! This place is packed even at 11am and for good reason – everything about the meal was great. Lastly, cocktails at the Signature Lounge in the Hancock Tower are the perfect way to end a long day of sightseeing and if you go right at Golden Hour, you are rewarded with incredible views. If you make a reservation for dinner you do not have to wait in line, but if you are just going for drinks make sure you go early (there was even a line at 4pm), but it moves pretty fast.

chicago signature lounge

Give yourself enough time to see the sights.

There is a lot to see in Chicago (and even more when you travel with a photographer!), so make sure you give yourself time to see all the city has to offer. We went over a long weekend and the third day gave us much-needed extra time, but still not enough (sorry Art Institute, we will catch you next time). Architecture is one of Chicago’s claims to fame and the Architecture Boat Tour is a great way not only to see many of the architecture types, but to have a professional explain it to you. You also get to experience one of Chicago’s greatest attributes, the river. Millenium Park and the Bean are another must for first time visitors and if you are lucky enough to go later in the night, you can even see the attractions without the hoards of visitors who visit during the day. Navy Yard was another place worth a visit for the great views of the city, but was quite crowded over the weekend.


Evening activities should include a trip to Second City where Bill Murray and Tina Fey are just two of the numerous alumni, and the Improv All-Star Show certainly had us laughing. A trip to a jazz and/or blues club is another must, and visiting B.L.U.E.S on Saturday night was the highlight of Max’s trip. There are no frills or fuss about this place, but our draft beers and corner seats just added to the ambience.


There is never enough time to see everything a city has to offer, but we felt we had a good amount of time to blend sightseeing with some fun activities, giving us a great feel for the Windy City. Beautiful spring weather made the visit more enjoyable and I would highly recommend spring or early fall as the best times to squeeze in a long weekend in Chicago.

Have you been to Chicago? What are some of your favorite things to do there?

Photo Credit: The Talented Max Holiver @ Max Holiver Photography 

13 Comments Post a comment
  1. Sounds like the perfect weekend celebration! When we move back I think a food tour of Chicago is a must! xoxo

    August 24, 2015
    • I could not agree more – sounds like the perfect plan! Lots more stateside exploring to do when you return!

      August 25, 2015
  2. Fabulous itinerary and photography!

    August 24, 2015
  3. Love this post filled with many of Chicago’s great sites to see! We can’t say enough good about the Architecture Tour. We expected a boat passing by a few nice buildings, but the very knowledgeable guide we had could teach in college! Want to go back to Chicago, for sure.

    August 24, 2015
    • Thank you, Bert and Rusha! I could not agree more about the architecture tour. The guides make the whole tour worth it! It is certainly a city I could keep returning to as well!

      August 25, 2015
  4. Bernie #

    Missed your blog, Bridget! Welcome back! The photography is fantastic!

    August 24, 2015
    • Thank you, Bernie! I agree on the photography wholeheartedly. Max gets all the credit for this one!

      August 25, 2015
  5. I’ve only visited Chicago once when I was a little girl so that doesn’t count! Definitely bookmarking this hotel. Hopefully I can visit the Windy City in 2016.

    Happy travels 🙂

    August 24, 2015
    • That is how I felt, Lauren! I definitely needed to go back as an adult and experience it again. Hopefully you can make it there next year!

      August 25, 2015
  6. I’ve heard great things about Chicago and you’ve just given me a lot more reasons to go visit. So now it’s on my great US cities to visit list!

    November 12, 2015
    • Thanks, Suzanne! It is often overshadowed by the likes of New York and San Francisco, but it is such an amazing city! There is lots to see and do outside too which is great.

      November 13, 2015

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