Chicago City Guide: 48 Hours in Chicago

Hook, Thread & Tinker Chicago City Guide - 48 Hours in Chicago Chicago Skyline at Sunrise: Photo by Dave Wilson

This post is a continuation of my Chicago City Guide series. So far we’ve covered:


Unless you visit often, I know that it’s hard to figure out what to do on a short visit to the city because there is SO MUCH to do. Chicago is an amazing city – having a lot to do is a good problem to have – it just means that future visits are necessary.

I have a list of suggested things to do if you have a weekend to spend in Chicago. You’ll note that a couple of the activities may be seasonal, but Chicago is a great city year round, so don’t shy away from the cold temps!

Day 1 (assumes mid-day start):

Head to your hotel and ask for a map of the area – downtown Chicago is very walkable if you’re up for it. If you’re not up for walking or if you’re visiting Chicago on a budget I recommend spending a few minutes getting acquainted with the trains and buses in the area.

Insider Tip: Chicago streets are marked using a grid system. If you know where Lake Michigan is you always know where East is. 

Grab lunch at Portillo’s on Ontario – it’s worth a quick walk out of your way for an Italian Beef sandwich or hamburger (vegetarian options also available!).

In warmer weather, head over to the river and grab your pre-purchased tickets for the Architectural Boat cruise or walk South down Michigan Avenue to the Art Institute.

Stop into Garrett’s popcorn for some Chicago Mix (grab extra napkins!) on your way to or from either place.

Head back to the hotel to freshen up before dinner.

Enjoy dinner at a number of spots, but I would recommend booking reservations at Chicago Chop House or Bavette’s for nice steak.

From dinner, hop in a cab (or use Uber) or take the Red Line North to the Green Mill for authentic jazz music.

Hook, Thread & Tinker Chicago City Guide - 48 Hours in Chicago Cloud Gate – Millennium Park: Photo by Dhilung Kirat

Day 2:

Get an early start and begin your day with a donut from Glazed & Infused.

Hop on the bus from Michigan Avenue and head to the Museum Campus for the AquariumPlanetarium and/or Field Museum. If you are traveling with children (or if you’re a kid at heart), the Museum of Science & Industry is an awesome place to spend a few hours.

Head to lunch at a local pizza spot– I recommend either Lou Malnati’s or Coalfire depending on what you’re in the mood for.

If it’s warm, take a walk through Millennium Park (and maybe stop in at Fannie May candies for a mint meltaway or pixie). If it’s a bit chilly, enjoy the shops on State Street and Michigan Avenue.

Rest your feet for a few minutes and freshen up for a delicious dinner at Au Cheval or Longman & Eagle, but don’t forget that these restaurants do not take reservations. Get there early so that you don’t have a long wait!

From dinner, make your way to your late show reservations at Second City.

On your way back to your hotel stop in for a quick drink in the Signature Room on the 95th floor of the John Hancock building (the best view of the city is from the women’s restroom!).

Day 3 (assumes 1/2 day):

Start your day early and head straight to The Bongo Room for an amazing brunch.

On your way back to the hotel, rent a Divvy bike and take advantage of Chicago’s beautiful lake bike path or, if you’re traveling with kids, check out the Children’s Museum at Navy Pier before packing to head home.

Don’t forget to check out some of my insider tips from my Chicago City Guide posts when deciding exactly what you want to do on your weekend in Chicago. As always, if you have questions or suggestions, let me know in the comments!

p.s. The Freshly Picked moccasin giveaway ends tonight – have you joined in?

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4 thoughts on “Chicago City Guide: 48 Hours in Chicago

  1. You hit it spot on! While I haven’t been to those Chicago steak places, I definitely like all the recommendations. I think one of the first spots I went to rather than steak was Cafe Ba-ba-reeba for tapas. I like it because it is a nice restaurant and can be on the lower end of pricing compared to a longman eagle.

    It is so hard to choose! I do love Girl and the Goat as an option too, but then I end up spending way too much in a weekend going to all the nicer/higher end places so always good to break it up 😉

    Ok now I am hungry!

    • Ha – so true re price. So maybe I should have said to leave your diet and budget at home :).
      I forgot about Cafe Ba-ba-reeba! Thanks for the add!!!

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