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Chicago in 2 days with theater, architecture, drinking, tours, comedy, and pubs, Coldplay, cocktails, and a river tour

Updated on July 26, 2016

How to plan and make the most of your stay

Okay, before I take any trip, I do my homework. There is no reason to walk aimlessly when you have a limited amount of time to enjoy your stay. My best friend ahead of my Chicago trip was a copy of Lonely Planet's city guide. It is full of maps and cool tips. Although there are a few websites that seem useful, watch for their agenda. There is no reason to pay more for anything than you have to.

Ahead of time I booked our stay though AirBnb for $420 for an apartment in Lincoln Park for 3 nights. It is a quiet, safe neighborhood and I thought this was a bargain. I'll get to it below, but we also prepaid our parking----$45 for 3 nights and days through Spothero, bought our tour and show tickets ahead as well.

One of Chicago's cool public artworks
One of Chicago's cool public artworks

Day 1 ---Friday Night

We drove in from western New York for our stay. On paper, it was supposed to be about an 8 hour drive, but construction in Indiana brought us to a crawl. Although I should have known this ahead of time, we gained an hour in the Central Time Zone and made our dinner reservations.

Arriving in Lincoln Park was easy. We had our parking spot in a garage and simply had to scan our receipt for entry. The Airbnb apartment had easy directions and entry. I was pleased to find a clean, spacious spot for our weekend.

We made reservations for Tapas at Cafe BaBareeba. Awesome! Sampled everything and made it out under $100. From there we walked to our 8pm Second City show. We sat right by the stage and laughed our tails off. Now I figured it was time for a nightcap, so we walked a block to Old Town Ale House and had a few cocktails and ogled the racy artwork on the walls....Interesting to say the least. After that, we used Uber and were back to our place in less than 10 minutes.

LIncoln Park, Chicago, IL

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Day 2

Ok, so we have a full day so I planned this out well...or so I think.

10am- Chicago Crime Tour----Cool narrated tour of the city's Capone days. $25 each

After the tour, we hot a "Hot Tickets" location and bought half price tickets for a play near our place. Wandered a block and got ourselves a Chicago Hot Dog and a Strawberry Cheesecake cupcake at the Hershey store.

2 pm-Tour of Frank Lloyd Wright's Robie House. Great architecture. $17 each

5 pm- River tour of Chicago's architecture. We learned a lot while having a few Goose Island brews on the boat. About 90 minutes. $65 total

8pm- Play time. The theater was 3 doors down from our apartment and was quite entertaining..."The Portrait" based on Klimpt. $55 for 2 tickets

After the play---Uber to Kingston Mines for BBQ and Blues. There was a $15 door. I ordered a bucket of Blue Moons and a sampler platter. Although the two stages went to 5am, we didn't quite make it that late.

Too much? Naah....we loved every minute of our day.

Second City for Improv
Second City for Improv
Chicago Hot Dog
Chicago Hot Dog

Day 3

So, on our last day my wife and I split up for the morning. She didn't have much interest in taking a tour of Wrigley Field with me and I didn't have too much interest in going to the Art Institute of Chicago with her.

11am- Guided Wrigley Field tour. Although I wish the Cubs were in town, this was cool. The tour took you into the visitor's locker room, the pressbox, and all over the stadium. At the same time, my wife was able to leisurely stroll the museum without my fidgeting.

I took the Red line downtown and bellied up to a Moscow Mule in Miller's Pub. Cool place with great woodwork. I figured that I would let the wife take her time, so I had to get a "Cheezburger" at the Billy Goat. Washed it down with an Old Style.

Met up by the lion statues out front and wandered through Millenium and Grant Parks to see the cool public works.

Now....Deep dish pizza time at Giordino's downtown. It was a true work of beauty!

Now, we had tickets for Coldplay at Soldier Field, so we decided to head back to the apartment to put our feet up for a bit. Good choice.

We bought an all day Metra pass for $10 each and found it very useful for this day. Although it may need another page, the show was awesome!

Home of the Cubbies
Home of the Cubbies
Pre show "fireworks"
Pre show "fireworks"
Coldplay's Yellow
Coldplay's Yellow

Last morning

Monday morning and it was time to head home. Getting out of the city was no problem and scanning the parking pass to leave was easy. We left stuffed and happy!


It may sound like this was over-planned, but I disagree. When your time is limited, make the most of it!


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