Weekend Guide to Chicago

Weekend Guide to Chicago

If you’ve seen my Phoenix, AZ guide, you know I love to show people around places I love. Probably the most-often-asked question of me is “how should I spend a weekend in Chicago?” After all, Chicago is THE best place to visit (I might be biased), and spending time here should be on everyone’s list. After having many, many weekend visitors over the past few years, I think I have this tourist thing down pat. Here’s my weekend guide to Chicago:

Weekend Guide to Chicago

Friday Night

You’ve just arrived in Chi-town and you are STARVING. I get it. This shouldn’t come as a shock, but you just need to start with deep dish pizza.

My personal favorite is Lou Malnati’s, but Chicago has pleeeenty of different deep dish offerings. I like to tell people this: if your favorite part of regular pizza is the crust, go to Lou Malnati’s (and get the butter crust). If you’re more of a cheese person, go to Giordano’s (whose pizza can only be described as cheese casserole). If you can’t get enough tomato sauce, you have to check out Pequod’s in Lincoln Park.

After you’ve gotten your deep dish fix, roll yourself on over to a comedy show. Chicago is famous for its improv and sketch shows, and I recommend both The Second City and IO Theater. Both are in the Old Town/Lincoln Park area. I couldn’t pick a favorite club–just read reviews of specific shows before you book.


Grab brunch somewhere in the Gold Coast. I like to recommend the Three Arts Club Cafe at Restoration Hardware, even though I myself have not been yet. There is definitely bound to be a line, so try to get there somewhat early (they open at 10am on Saturdays and Sundays).

After brunch, walk down Dearborn St. to State St. You’ll be in the heart of the Gold Coast, which is one of Chicago’s fanciest neighborhoods. Stroll down Rush St. and you’ll see what’s basically the Rodeo Drive of Chicago–the nicest designer stores are here. From there, head East to the famous Michigan Avenue. Michigan Ave is where the rest of the world likes to think Chicago does its shopping. Head south on Michigan Ave so you can experience the Magnificent Mile and you’ll find yourself face to face with The Bean.

Weekend Guide to Chicago

The Bean is a staple of Chicago’s landmarks, and, I have to admit, is pretty cool. Take some selfies, and then explore the rest of Millennium Park. There are a handful of cool things to see there, including artwork, the Lurie gardens, the Jay Pritzer pavilion (kind of looks like a cornucopia), and the Crown Fountain (those pillars with moving faces on them).

Weekend Guide to Chicago
Millennium Park as seen from Cindy’s Rooftop

It’s also worth going up to Cindy’s Rooftop inside the Chicago Athletic Association. Cindy’s offers amazing views of Millennium Park and Lake Michigan!

Weekend Guide to Chicago

When you’re done exploring this area of town, hop on a Chicago Architecture Tour. If you do ONE thing in Chicago, this must be it. I’ve been on so many Architecture Tours myself at this point, and they just never get old. You get to boat up and down the Chicago River and learn all about Chicago history and architecture. I can’t recommend it enough! Two of my favorite companies are Wendella (more of a cruise) and Seadog (speed boat that takes you out on Lake Michigan as well).

Weekend Guide to Chicago

If you have time, check out the Art Institute of Chicago. It’s one of my favorite museums in the world. I also recommend taking a tour with Museum Hack – they offer interesting tours of the Art Institute and you learn more than you normally would at the museum. Plus their guides are hilarious.

After activities, refuel with dinner!

Weekend Guide to Chicago
Siena Tavern. YUM.

There are a ton of great places to get dinner in Chicago, but if you are visiting you MUST try to get a table at the famed Girl and The Goat. It’s hands down the best meal I’ve had in my life, every single time. If you book your trip early enough, you’ll be able to get a table (use OpenTable or give them a call). You definitely need to make a reservation well in advance (like, months). If you can’t get into Girl and the Goat, other favorites are Sunda (Asian infusion), Cafe Ba Ba Reeba, Gilt Bar, Beatrix, Little Goat, and Au Cheval. Click here for my full list of all the best restaurants in Chicago!

Weekend Guide to Chicago


Get out of downtown and explore one of Chicago’s many neighborhoods! For first-time visitors, I always recommend visiting the famous Wicker Park. There are plenty of shops, restaurants, and bars, and you could spend all day there.

Weekend Guide to Chicago
Jeni’s Ice Cream, with locations in Wicker Park, Lakeview, Old Town, and Lincoln Park

If you’re visiting Wicker Park during the summer, go put your name down at Big Star. This is a Chicago favorite, with a huge patio, delicious tacos, and refreshing margaritas. While you’re waiting for your table to be ready, go shopping around Damen and Milwaukee avenues! There are tons of interesting stores, AND a Jeni’s Ice Cream. Yes, I’m suggesting you get dessert before lunch.


If you can squeeze it in…

Go to a Cubs game. Tickets can be kind of pricey these days ever since their World Series win in 2016 (best year ever), but the experience of catching a game during the summer just can’t be beat. Grab a beer and a hot dog, bring sunscreen, and you’ll be set for the day. It’s truly one of the most local experiences you can have.


Getting Around Chicago and Safety

Chicago has one of the best public transportations systems in the country (aside from New York). You can take a bus or train to get almost anywhere! Ubers/Lyfts are also plentiful, and not too expensive unless it’s surging.

I personally do not take the El (train) after ~9pm by myself. It can get a little seedy, BUT the bus system is generally very safe. I have taken the bus home from the bars at 2am before with no problem (but if you’re my mom or dad, you didn’t read that).

It’s very easy to feel safe in Chicago, especially if you’re in touristy areas on the North Side. However, remember that crime happens in all big cities and you need to be aware of your surroundings. When it comes to getting around, it’s always better to be safe than sorry with Ubers/Lyfts/cabs.


Any questions? Something I missed? Comment below! Enjoy Chicago!

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