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Our World Wind Weekend in Chicago

When Ryan’s birthday rolls around, I hate buying him “stuff”. I prefer to buy experiences – things we can do together, places we can go, a new adventure. So naturally this year I bought him a trip to Chicago. Our beloved Wisconsin Badgers were going to be playing a football game at Soldier Field and while I hadn’t planned to attend the game, I thought hanging with other Badger fans and check out a new-to-us city could be fun. We’ve almost fully recovered from our Las Vegas trip so why not go? We stayed in the South Loop which had a great mix of restaurants and bars that were all walkable from where we were staying.


Our biggest regret of this trip was not getting authentic, deep dish pizza. However, we did go to Roots for the yummiest taco pizza I’ve had in a long time. I am an absolute pasta fiend, so Friday night we decided to hit up Bar Siena for pasta. They had an adorable setup for outdoor dining and we loved the vibe there. It’s in a fun neighborhood and is walkable to lots of bars and restaurants. We also love sushi, so Saturday night we went to Sumi Japanese Restaurant, which was near our hotel and highly rated. It was quality sushi if you’re looking for a casual and affordable sushi stop I couldn’t recommend this more.

Taco pizza at Roots


We like to check out local spots where regulars like hanging out. Friday night after dinner we went to Federales. My sister had been here a few times and told us that they serve tequila shots in ice shot glasses and then you chuck them at a big bell and everyone cheers, so obviously we HAD to do that. We hung out for a few drinks at Burger Bar Saturday night and the bartenders recommended Kasey’s Tavern and First Draft in the South Loop, both of which we hit up. Ryan loved the beer selection at First Draft especially. A few other memorable stops for us for drinks were Cruz Blanca Brewery – a great mix of brews for Ryan and margaritas for me. We also stopped at Haymarket Pub & Brewery where we split a great sandwich and I had the tastiest strawberry basil seltzer.

Strawberry basil seltzer at Haymarket


We didn’t do a ton of touristy things while we were there but we do love hitting up craft breweries when we check out new cities so we got tickets to The Barrel Run. They drove us around in a bus that looks like a barrel and we stopped at Lake Effect Brewing Company, Goose Island and Great Central Brewing Company. We also took our obligatory pictures at The Bean.

The Barrel Run bus

It was a quick trip but we had such a great time that we’ve decided to get back to Chicago again next year. It’s only an hour flight from St. Paul, so there’s no reason why we can’t get back and finally get that deep dish pizza! What’s your favorite thing to do in Chicago?

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