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Chicago Travel Guide

Chicago Travel Guide

Why I Love Chicago

Micah is based in Chicago, so the last couple years this has felt like our second city. It’s often where our adventures begin and end, and it’s the city we jet off to when we have a night or two to spare.

First, Chicago is absolutely beautiful. The elegant, diverse architecture juxtaposed with the rawness of the raised “L” train tracks creates an atmosphere that is uniquely Chicago. The museums are some of the best you’ll find (don’t get me started on the Art Institute—LOVE), there are amazing restaurants every few steps, and it’s possible to experience this city on a budget.

I have written several blog posts about our Chicago trips, but I thought I would make a more boiled-down travel guide for easier access to all my favorite recommendations. I will keep updating this guide as we continue to visit this city we love.


Hampton Inn Chicago Loop Near Michigan Avenue

This is our favorite hotel that we have stayed in (we’ve stayed here at least three or four times now). It’s in a perfect central location, clean, beautiful, and has a nice complimentary breakfast.

Cambria Chicago Loop

We stayed here last June when our favorite Hampton Inn was a little too expensive, and it was in an equally convenient location, clean, and beautiful. The only downside is there is no complimentary breakfast in this hotel.

Holiday Inn Rosemont Chicago O’Hare Hotel

If you are looking to save a little money, staying in a hotel near the O’Hare airport is a great option. The rates are less expensive than the hotels downtown, and you could take a hotel shuttle to the airport and then jump on the Blue Line from the airport to head downtown, which is about a 45-minute train ride from the airport to downtown. We have done this multiple times, and this Holiday Inn is a nice hotel option.

Coffee Shops/Take Out



The best coffee I’ve ever had. It’s expensive, but so smooth and delicious.

Doughnut Vault

An adorable stop that’s only big enough to fit a cash register. These donuts are big and delicious. A must.

Protein Bar

A fast-food health chain we recently tried and loved. They offer breakfast and lunch options, as well as smoothies. Their buffalo chicken wrap is delicious, as well as their breakfast wrap and egg scramble bowl.



I know this may seem uncool because it’s so obvious, but this is truly our favorite deep dish pizza. Don’t waste your time anywhere else.

Girl and the Goat

A unique tapas-style restaurant—one of the most impressive meals I’ve ever had. Call ahead for a table or take a seat at the bar.

(Click here for the ultimate Chicago food guide.)


The Signature Lounge

This is a must stop for us. Located on the 96th floor of the John Hancock Building, you won’t find a better view in town or a better Spiced White Russian. Trust me, you have to come here.


Andy’s Jazz Club

A fun new find with great cocktails and live jazz music. A friendly and accommodating environment.


The Art Institute of Chicago

My absolute favorite museum. You are going to see a little bit of everything here: Picasso, Monet, Van Gogh—be prepared to get lost for hours (and here’s a tip: don’t waste your time with the paperweights and photographs of string in the lower level of the museum—just trust me on this one).

Make sure you download the Art Institute of Chicago app on your phone and take headphones. It’s a free guided tour and just as good as the paid guided tour the museum rents.

Field Museum

You will be amazed by the towering dinosaur fossils. You have to experience this museum.


Adler Planetarium

A neat museum than can be toured in two hours or less. I suggest getting tickets for the constellation show. Worth seeing, but make sure you visit the Art Institute and Field Museum first.

Museum of Science and Industry

This is a fun museum with different exhibition options, including a tour of a real German submarine that was captured by the U.S. Navy during World War II, as well as a tour of a real (non-working) coal mine. If you have kids, I highly recommend bringing them to this museum.


The Magnificent Mile

As much as I love shopping, my shopping game has been pretty lame on our visits to Chicago so far. We have been too busy experiencing the museums so far to spend too much time finding unique shops outside of Michigan Avenue (a.k.a. The Magnificent Mile). With that said, Michigan Avenue is a lot of fun. There are a bunch of really expensive stores, but trust me when I say you should go in for the experience. We have been in stores like Omega and David Yurman, and we have yet to meet a sales person who was snooty or pushy, and they always offer you water (sometimes even champagne) and give you space to look.

Essential Sites

Millenium Park

A must visit to see Cloud Gate (a.k.a. The Bean) and take a mirrored selfie. There is also an outdoor theater for concerts and beautiful gardens to wander through.

Navy Pier

Catch a ride on the iconic ferris wheel or enjoy a hot dog and beer lakeside. This is also the launching point for sailboat tours.

Summer Activities

Divvy Bikes—Chicago’s Bike Share

Unless the city is under a thick blanket of snow, we always rent Divvy Bikes. They are easy to use, there are many stands to find and park them, and they are reasonably priced. Chicago is also one of the safer feeling cities to ride a bike (in my opinion, anyway).

Tall Ship Windy Chicago Sailboat Tours

Tall Ship Windy offers several different sailboat tours, including a pirate tour, an architectural tour, and a fireworks ride on the Fourth of July. The city is magical from this vantage, and refreshments are offered for sale during the ride. They even take volunteers to help raise the sails! This is one of the most fun things we’ve done in Chicago so far—we will definitely take another tour just to ride on a sailboat again.

Chicago Cubs Game at Wrigley Field

This may go without saying, but if the Cubs are playing when you’re in town, you really should try to catch a game at this beautiful stadium. The atmosphere is so fun. Make sure to order a Chicago-style hotdog.

Winter Activities

Ice Skating at Maggie Daley Park

If you’re in Chicago during winter, you must do this (even if you’re a shaky skater like I am). The loop provides you with incredible views of the city—a perfect date with your sweetheart.


Summer Packing

No matter what time of year, including in the summer, you want to make sure you always have at least a pair of pants and a jacket. The nights can be chilly and every now and then you will get a random day in the low 60’s. You will never regret packing layers. Oh, and wear comfortable shoes. This is a city you want to walk around in, so ditch the heels or really flat sandals. Wear something you can walk in for miles or you may be limping the next day (been there).

Winter Packing

In the winter, you need to dress for the arctic—not even kidding. The winds are absolutely brutal when combined with sub-zero temperatures, but if you have an extra warm jacket and boots that keep your feet dry, walking around a snowy Chicago is so much fun. Jeans, snow boots, a thick down jacket, scarf, hat, and gloves will suffice—Micah and I never found the need for thermal pants underneath our jeans. Oh, and keep a packet of tissues with you.

I hope you find these recommendations helpful! I will continue to add and update with each new visit to this city we love. Do you have any Chicago recommendations? Leave a comment below!

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