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Chicago, Illinois in 2 Days

Guest post by asieracki

Map tips: each color represents a different day. Click a marker to learn more about the spot, and click the star in the map header to save the entire map under Your Places in Google Maps.

Day 1

  • Tontas
  • Warwick Allerton Hotel

We drove from Cleveland (about 6 hours), and with the construction on the freeway, all we had time to do was grab dinner at Tonta’s. We ate on the rooftop, which is walk-in only and fills up fast. They have Peruvian food and we ended up splitting a lot of smaller dishes as there was a lot we wanted to try. The food was great and I definitely recommend the rooftop if you can get it. We stayed at the Warwick Allerton Hotel, which is right on the Magnificent Mile. While I do recommend staying that close as you are able to walk everywhere, parking is $60 a night.

Day 2

  • Yolk
  • After-Words New and Used Books
  • First Lady of Chicago Architecture tour
  • Giordano’s Pizzeria
  • Museum of Contemporary Art
  • Shaw’s Crab House
  • Green Mill Cocktail Lounge

We started at Yolk for breakfast They have a big menu, big portions, good food. They were quite busy but had seating at tables, the counter, or outside, so the line went quick. Walked to After-Words New and Used Books and browed while we waited for our First Lady of Chicago Architecture tour. We bought tickets in advance, but you can buy at box office there but you never know how busy they’re going to be. The tour took us down the Chicago river by boat (90 minutes long) and they explain all the buildings and towers and how things have changed over the years. The architecture portion was slightly interesting, but the best part for us was just going down the river and seeing the city.

After the tour, we headed to Giordano’s (recommendation by Beau) for lunch. They were crazy busy but the deep dish pizza is so worth it. They recommend you order your pizza 45 minutes in advance (not a typo) because it takes so long took cook. However, if you do that by the time you’re seated it’s like they bring the pizza right out!

As it was over 90 degrees outside so we opted for an indoors activity and headed to Museum of Contemporary Art. We weren’t blown away by it but it was kind of cool. After wandering around the Magnificent Mile and showering, we Ubered to Shaw’s Crab House for dinner – we could have walked but it had recently started raining. Good food and cool ambiance. Particularly suggest this place if you are a lover of seafood.

We took another Uber to the Green Mill Cocktail Lounge, a jazz lounge, that used to be one of Al Capone’s old speakeasy clubs. There’s a “trapdoor” to the basement behind the bar where extra liquor is kept. Unfortunately only the staff can go down there, but if you sit at the bar you can sneak a peek! The décor and interior is still authentic and there’s definitely a 1920s vibe to everything – even the cash register. There was a $15 cover charge for the band that was playing (sometimes it’s less but worth the $15) and they only take cash. They take jazz very seriously and you have to be quiet while the band is playing. One guy next to us was too loud and after a few warnings, they kicked him out. It was very crowded so unless you don’t mind standing, I suggest getting there EARLY.

Day 3

We were going to go out to breakfast before heading back, but we ended up waking up so early that we opted to just head back instead of sitting around waiting for the restaurant to open.

Traveled in July 2016

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