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A Long Weekend in Chicago – Day 1

With a flight from the Twin Cities taking only about an hour, Chicago is a great getaway for a long weekend. Although, you could spend twice that amount of time there and not even scratch the surface of this cool town. I’m here to share how my friend and I spent 3 days in Chicago. I hope this gives you a good taste of all there is to do!
How to Spend a Long Weekend in Chicago - Due Midwest

We found a cheap flight on Southwest which got us in got into the city on Saturday evening and going home late Tuesday night.  We decided not to stay in a hotel downtown and instead found an AirBnB in Lincoln Park which turned out to be a great home base. I’ve stayed downtown in the past and while it’s convenient to some of the attractions, you miss out on the local vibe. Where we stayed was only about a mile walk from the brown line stop of Armitage. Regardless of where you stay, make sure it’s close to an “L” stop (L stands for elevated train). The L goes everywhere and makes getting around super convenient. We decided to buy a 24 hour pass which lets you ride unlimited for, you guessed it, 24 hours. Since we did a lot of exploring, this was a great deal at only $10. We ended up getting one for the first day and then bought a second the next day.

When we got off the plane, we looked out the windows to see sideways blowing snow (!) which meant we took an Uber. It was surprisingly cheap for a 45 min ride. I think we paid about $35-40. My brother used to live in Chicago and suggested we try Pequod’s Pizza which was conveniently in Lincoln Park. We didn’t grasp the popularity of this place plus it was a Saturday night so needless to say, we didn’t get a table. We vowed to try another day so more on that later. We ended up at Beer Bistro which was a good pub food place. We had a nice dinner until we were invaded by Syracuse fans there to watch the Final Four game. We decided to leave the rowdiness behind and ended up at the Arrogant Frog bar which was awesome! It had a great atmosphere and a cute bartender to boot 😉 We had a few too many drinks and made our way back to place to rest up for the fun planned for the next day!
How to Spend a Long Weekend in Chicago - Due Midwest

Day 1: 

Wake up early (or sleep in if that’s your jam) and grab yourself some brunch! Chicago has more delicious restaurants than you can shake a stick at so just close your eyes, point and pick one! We walked down to Eleven Lincoln Park which is a diner/deli. I got some sort of cheesy Mexican egg dish and it was so so good. Highly recommend the food and the atmosphere! The place was bumping on a Sunday morning so make sure to call ahead if you plan on going here.

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After stuffing ourselves silly, we walked to the Lincoln Park Zoo and Conservatory. This is a smaller, city zoo which was a perfect size for a couple of hours of wandering. I would say we spent about 2-3 hours here and saw the whole place. The conservatory was gorgeous, they had some really cool animals and the grounds were lovely. Definitely recommend checking it out! Oh, and it’s free! Can’t beat that. 🙂


How to Spend a Long Weekend in Chicago - Due Midwest
How to Spend a Long Weekend in Chicago - Due Midwest
How to Spend a Long Weekend in Chicago - Due Midwest
How to Spend a Long Weekend in Chicago - Due Midwest
Make sure to head just outside of the zoo to the nature boardwalk to get a great view of the skyline!
How to Spend a Long Weekend in Chicago - Due Midwest

How to Spend a Long Weekend in Chicago - Due MidwestAfter the zoo, we were still full from brunch but needed a little snack 😉 Right across the street from the zoo we found a great little French patisserie called Vanille. You may want to go with a friend just so you can try one of every flavor of macaron. Or, just buy one of each and “save them for later”. I won’t tell. I tried passion fruit mango, red velvet and salted caramel. The salted caramel was amazing and beat out the other two by a mile. What was cool is she broke one of the passion fruit ones so I got an extra free. Gotta love that kind of service! I also got that brownie/piece of fudge/square of heaven with gold on it you see below which I think was called the Royal. There were several layers of deliciousness in there but it was super rich. Don’t be like me and try to eat it after a giant cheesy egg brunch…
How to Spend a Long Weekend in Chicago - Due MidwestHow to Spend a Long Weekend in Chicago - Due Midwest
We made our way to Millennium Park to check out Cloudgate aka the Bean. If you can pick which day you see it on, pick a sunny one with blue skies. It looks so cool shining there in the sun with an electric blue sky reflected in it. As you can tell from the pictures below, you won’t be alone there since this is a big attraction. However, you get GREAT views of the skyline and it is pretty much a must see. You will also get the added bonus of tons of stranger selfies in all your photos. Win win. There are more sculptures in Millennium Park than just the Bean so be sure to wander around the rest of the park too!
How to Spend a Long Weekend in Chicago - Due Midwest
How to Spend a Long Weekend in Chicago - Due Midwest
How to Spend a Long Weekend in Chicago - Due Midwest
How to Spend a Long Weekend in Chicago - Due MidwestWe headed over to the Magnificent Mile which is another name for a section of Michigan Ave which is lined with every store from Coach to Zara to a giant Louis Vuitton. There are lots of places to shop and also huge crowds. This area is definitely worth a wander if you want to do the former and don’t mind the later. Unless you stay downtown, you will have to go into the “Loop” or downtown area to change lines on the L so you could always fit this in between your other adventures.

How to Spend a Long Weekend in Chicago - Due Midwest

While walking down Michigan Ave, I saw a building that said it was the public library on the outside. Since I love old libraries, we decided to stop in. You guys, this building is INCREDIBLE! Two huge and gorgeous glass domes, carved wooden banisters and mosaic tile as far as the eye can see. The old saying “They don’t make them like they used to” totally holds true here. Look at this place!
How to Spend a Long Weekend in Chicago - Due Midwest
How to Spend a Long Weekend in Chicago - Due Midwest

We weren’t in the mood for shopping or crowds so we decided to skip the rest of the Magnificent Mile. Instead, we headed over to a neighborhood called Wicker Park to browse around. This cute neighborhood (adjacent to Lincoln Park) was much more our speed since it has more local boutiques and lots of interesting restaurants. You’ll also find some familiar names like Urban Outfitters and Walgreens here too. When I travel, I always prefer to check out areas where it’s mostly locals. This is where the stores you won’t find anywhere else are and you get to avoid all those “touristy” tourists. Because, that isn’t you! You are a cool, hip tourist that digs the local vibe. Maybe you’ll even get mistaken for a local 😉 The easiest way to get there is hop on the blue line and get off on Damen.

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A couple places we stopped in Wicker Park worth mentioning are Myopic Books and Stan’s donuts.  Stan’s donuts is literally right off of the L stop, you can’t miss it. Plus, there was a line out the door so you know it’s good. Any place that’s really busy in a town with this great of food will be worth it! I’d eaten here the last time I was in town and all the donuts I tried were awesome. See what I mean below… Myopic Books is a wonderful, crowded maze of books. I loved it! Since I couldn’t go home with a suitcase full of books, I had to restrain myself from buying everything. If you want to spend hours or even 5 minutes inhaling that wonderful old book smell, check this place out!
How to Spend a Long Weekend in Chicago - Due Midwest
How to Spend a Long Weekend in Chicago - Due Midwest

Phew! By this point we were walked out and decided to venture back to “our” neighborhood for a bite to eat. We just stumbled upon Butcher and the Burger on our walk back from the L and it was so delicious. Such is the joy of the Chicago food scene. I sound like a broken record but it’s true! Check out my creation below. You only have to mutter the words “pretzel bun” and I’m putty in your hands.
How to Spend a Long Weekend in Chicago - Due Midwest

Stayed tuned for day 2 and 3 tomorrow! Another action packed itinerary awaits!

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5 Comments

  • Reply Due Midwest - A Long Weekend in Chicago – Days 2&3

    […] I’m back to tell you more about how to spend a long weekend in Chicago with our day 2 and 3. If you missed day 1, check it out here. […]

    May 6, 2016 at 4:53 pm
  • Reply Kelly

    This is a great recap. We’re with you- we much prefer the pace of local neighborhoods.
    We’re attending a conference outside of Chicago this month and believe it or not I have never been to Chicago. We’re going to take a train from Schaumburg into the city for 1 day. Since we have limited time, we’ve scheduled a Foodie Tour and a boat tour. Your post makes me want to make sure we fit in the Lincoln Neighborhood for sure!

    October 2, 2016 at 3:00 pm
    • Reply duemidwest

      I hope you have a great trip! I’m glad you found the post helpful. Chicago is definitely a great city. If you can squeeze in Pequod’s pizza, I don’t think you’ll regret it!

      October 11, 2016 at 2:17 pm
  • Reply Always a Foreigner

    Hey, I’m from Chicago and this was a great weekend you had! I second your recommendation of Pequod’s..either that or hometown classic Lou Malnati’s. Glad you had such a great time, Chicago is truly a wonderful city.

    March 3, 2017 at 6:55 pm
    • Reply duemidwest

      Great to get some approval from a local! We were able to pack a lot in! I think it was a good mix of touristy things and more local things. It’s why I love Chicago, there is so much to do!

      March 3, 2017 at 7:12 pm

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