Laura comes to Chicago! What to do with 48 hours

Travel storytelling is easily one of the best types of conversation. My best friend Laura recently returned home from a semester long adventure in Germany. From Facebook photos and brief conversations it sounded like she had a study abroad brochure worthy experience, but I wanted details. To hear defining moments, and to laugh at those ridiculous mishaps that every traveler experiences abroad. I wanted to hear her best meals and feel fierce food envy, and to learn the stories of the people she met.

But, instead of sharing all this with Laura, I went with a highly literate and convincing text inviting her to Chicago:

  – .*~.-ViSiT mEh iN cHiCaGo?!?!.~*.- oK sEe YoU oN tHuRzDay?!?.~.*-.*

 Somehow, the excessive punctuation and classic “s to z” substitution worked in convincing Laura because two days later, we met at the intersection of Adams and Clinton outside of Union Station in Chicago (you see – Laura interned in DC this summer, and my name is Reagan, so we have a very presidential friendship. We plan on getting each other an American flag lapel pin for Christmas.)

A true friend is when after 6 months of absence, laughter and conversation falls into the same stride we left off on.

Laura took a 4am train from St. Louis to Chicago, and I wanted to pick a restaurant that made her early trip worthwhile. The best Chicago has to offer and a great environment to sit and catch up for hours was the goal.

 After some serious google searching, I found just the spot, here we are at lunch:



A la 95th floor of the John Hancock building. This photo was in no way edited and no green screen was used. That is our view. Welcome, to the Signature Room on the 95th floor of the John Hancock Building.

As an American returning home, Laura saw “hamburger” on the menu and decided on that. Her first hamburger back in the states! I realized I was about to leave and ordered the same. My last hamburger in the states! Cheers to good company, good food, and breaking a new years resolution on day three.

Laura is a gifted traveler and lover of life. The best way I can describe our conversation is “stream of consciousness.” I’d ask the first thing that came to mind, and she’d share travel stories at the forefront of her mind. Laura would take off into the most hilarious, thoughtful, insightful, downright crazy and overall entertaining travel recollections. We’d laugh, casually look over our view of Chicago, then laugh some more.

I’m leaving for Europe in less than two weeks. When I return, I’ll have my own study abroad adventures to share. I can’t wait to again sit down with Laura, share my experiences, and have my first hamburger back in the states with her.

Travel tips for when your best friend spontaneously visits you in Chicago for 48 hours (an oddly specific scenario)

1. Hostel International Chicago
  • Great location near Millennium Park. A cheap overnight payment saves on travel time and cold metra rides to head out to the suburbs to sleep.
  • We had our own double bed room and a community bathroom.
  • Free breakfast in the morning. Laura and I talked to a student from Australia for an hour at breakfast. Great place to meet people and share ideas about what to do in Chicago.
2. Signature Room at the 95th for LUNCH
  • Very affordable lunch menu, great view. One of the best restaurants Chicago has to offer, especially for out of town guests.
  • Opt to have lunch at the Signature Room instead of visiting the Hancock Observatory- the observatory costs $15 and is often crowded with tourists, long lines, other photo-takers obstructing view ect.
  • The Signature Room on the 95th takes reservations (avoid any traffic and wait time) and meals cost about $14-$22, lunch and the view.
  • Near to the Watertower Place, Topshop,  Michigan Ave. and other great shopping options
  • Within walking distance of Millennium Park
3. Cosi on Michigan Ave. (across the street from the Art Institute of Chicago – very near the Bean)
  • For around $10 you can get a s’more plate (see below)
  • There is a two man table at the front window of Cosi. The BEST people watching in Chicago. Get a s’more plate, snag that table, and enjoy!
4. Second City Improv
  • Second City gives some tickets to and those tickets are sold at a discount. The show Laura and I saw on Thursday night was sold out on the Second City website, but hottix had tickets available, and at half the price! SCORE.
  • Some of my other favorite Improv and experimental theater options include IO – Improv Olympics and the Neofuturists. Both very affordable.
Day 2 Shenanigans with Laura
1. Always eat breakfast at the hostel (if available)
  • People are taller in the mornings. We are fresh woken up, ready for days to start. Good morning sunshine! Laura and I met some fun Australians at breakfast who were eager to hang out for the day (we declined because we wanted to continue catching up, but could’ve been very fun under different circumstances!)
  • When traveling alone, I plan on using breakfast as the place to find friends to adventure with.
2. Buy a day pass for the CTA
  • Costs $5.25 with unlimited rides. Worth it.
3. Chinatown for Dim Sum
  • It is a decent journey out to Chinatown. But, I really think one of the greatest aspects of Chicago is the diversity between neighborhoods. What better illustration of this than Chinatown?
  • Dim Sum at The Three Happiness is very authentic and delicious. Great for a light lunch or dinner feast, depending how you order.
4. Belmont – stop on red line
  • Always a favorite. Laura and I had many fun times here on St. Patricks Day and had good laughs walking around familiar streets.
5. Wicker Park / Bucktown
  • We took the blue line to Damen and enjoyed thrift shopping and boutique browsing.
6. Portillos
Comment on this post with any other Chicago destination suggestions!
Posted on by Reagan J Payne in Recommendations

2 Responses to Laura comes to Chicago! What to do with 48 hours


    Chicago food bargains:

    Hot Doug’s. So good and for the price it’s an ultimate steal. I had a Wagyu beef Cincy chili dog for about $7. that’s unheard of. With duck fat fries to boot. Talk about serious gourmet.

    In Water Tower, there’s a place called Wow Bao. Little dumplings for a few bucks. Not totally authentic but tasty and cheap.

    Lincoln Park Zoo is free. Farmer’s markets in Chicago are great too

  2. Reagan J Payne

    I need to visit Hot Doug’s!

    Devil Dawgs in Lincoln Park has fantastic, cheap, Chicago style hotdogs – nothing gourmet like Hot Doug’s, Can’t wait to try it out! Thanks for telling me about it!

    Next time you visit Chicago, definitely check out it has a listing of free events, concerts, and all the Chicago happenings!

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