Chicago Travel Guide

chicago travel guide

White Dress | White Sandals | Belt | Bag

Having just moved to Chicago, I still feel like I’m a tourist in my own city. But, that also means that all the tourist spots are fresh in my mind! Y’all asked me to share more about the Windy City so here we go. If you’re a first time visitor to Chi-town, here’s how to spend a weekend!

PS. Chicagoans have told me I can’t call it Chitown but I’m going to continue doing it until they stop calling California Cali.

Before I start, let’s get something out of the way. If you want to enjoy Chicago in all its glory, visit between June and September. Unless you are immune to the cold or have a fascination with snow, winter probably isn’t for you. Spring is too unpredictable and last year just consisted of thunderstorm after thunderstorm.

best view of chicago skyline


First things first, check into your hotel. Matt and I stayed at The Thompson for a little staycation back in July and it had a great location. Being centrally located and near Michigan Avenue is key! The hotel also has a cute restaurant called Nico which doubled as a swanky bar at night. The rooms were a good size and I about died over all the marble in the bathrooms. If you followed along on Instagram, than you know I did a photo shoot there with Simon G Jewelry. That post is coming in September so stay tuned!

There are so many hotels in the area that I’d recommend just finding the best deal. Chicago is very easy to get around using the train system but walking is so much easier. If you decide to stay in one of the surrounding neighborhoods, that’s totally fine – each one has a different personality. But for my first timers, you want to be right downtown.

For dinner on Friday, get yourself some Lou Malnati’s deep dish pizza. It’s the best deep dish in Chicago. Now, as a California girl, I feel like my life still would have been complete pre-Lou Malnati’s but many Midwesterners will tell you otherwise.


Dedicate one day to doing all the touristy things and one day to just enjoying Chicago life. I’d recommend seeing the sights on Saturday just so you can relax on Sunday! I always like to wind down the weekend on Sunday.

Grab breakfast at any of the following restaurants. If I’ve learned one thing since I moved, it’s that Chicagoans like to eat.

  • The Hampton Social. So cute and is home to the “Rosé All Day” sign. Loved the salad I got but am aware it’s a salad!
  • 3 Arts Cafe. Probably the most Instagrammed spot in Chicago. It’s so gorgeous but be prepared to wait!
  • Graze. This place is extremely casual as it’s part of a workout place but if you want an acai bowl, this is the place.
  • Left Coast. The location in River North just opened and we went there last week. It’s again, healthy food but it’s so delicious. They also have green juice!
  • Hash House. Your standard upscale diner with Chicago style serving sizes. Aka they are huge. They’ve got a giant menu and you can be sure to find something for everyone in your party. You go here to eat!
  • Longman & Eagle. I haven’t heard of a meal or drink they don’t do extremely well here. Add this place to your list whether you love brunch or bourbon.
  • Summer House. Definitely a place for Instagram photos. Super cute decor and ultra trendy. The food is decent!
  • Beatrix. It’s apparently amazing but we can never seem to make it there despite living 2 blocks away.
  • If you love Nutella, the Nutella Cafe just opened and it’s right near The Bean which is where I’d recommend starting your touring! Beware, the line is probably going to be long! I work right across the street and see a line at all hours of the day!

Walk through Millennium Park to catch glimpses of The Bean and the Jay Pritzker Pavillion. If you’re lucky, you’ll hear some musical acts practicing for that evening’s show. If you are in Chicago on a weekday, there are tons of free events here so make sure to google their calendar. There’s a little garden in between this Pavillion and the Chicago Art Institute that we walked through a few weeks ago too! There is this crazy fountain called the Crown Fountain that looks like a giant TV screen and has a woman’s face on it. It’s packed with kids in swimsuits waiting for her mouth to spew water in the summer – it’s a sight for sure.

If you are an art enthusiast, definitely check out the Art Institute – lots of different types of art for all kinds of interests. If you’re not into art or museums, don’t feel bad about skipping. We aren’t museum people usually and went once years ago and that was enough!

buckingham fountain in chicago

If you’ve got your walking shoes on, walk a few blocks south to the Buckingham Fountain. The home of Lollapalooza, this entire area is full of culture. This fountain is a little more refined that the Crown Fountain. If you’re really into getting your steps in, the Shedd Aquarium, Field Museum, and Adler Planetarium are a few very long blocks further south. If you want to save yourself some time, hop on the Red Line. I’d save these for another visit but if you’re into dinosaurs or any of the exhibits going on, take some time to see them.

Circle back toward Michigan Avenue and head down the main part to see the shops. The Burberry building is my absolute favorite! Stop by Dylan’s Candy Bar for a little sugar pick me up. Speaking of sugar, there is also a Sugarfina in the bottom floor of the Nordstrom and they have Pressed Juicery gummy bears right now! Yum! There are tons of restaurants for lunch and here are my favorites.

  • True Food Kitchen. Healthy California food. Pretty casual but we go there fairly regularly.
  • Sweetgreen for a quick bowl or salad.
  • Velvet Taco. A great spot to get some good tacos. They have the regular flavors as well as a few unique ones in there! And it’s also vegetarian friendly!
  • Howells and Hood. The food is average but the beer selection is pretty good! Might be better just for grabbing a beer!

view from john hancock tower

Chicago is also known for having some amazing views of the city from above. I’d recommend either going to the Hancock Building or Willis Tower – no need to do both. From a view perspective, the Hancock is better in my opinion because you can see the lake.

Tip: if you don’t want to pay the fee, just go to the Signature Lounge for a drink and the view is identical. The view from the women’s bathroom might just be the best in the whole place (weird, I know). If you’re dying to get a photo in the clear glass box at Willis Tower (see below), than swap out the Hancock for that. While both locations have 360 degree views, the box faces west and there’s not much to see that way.

chicago willis tower sky box glass deck

Before dinner, make your way back to your hotel to freshen up. People dress pretty casually here so don’t feel a ton of pressure to go all out. Be sure to make a reservation if there’s some place you’re dying to try – it’s very hard to make one the day of or even the week of. I’m still so surprised! Here are a few of my favorite dinner spots:

  • RPM Italian. The portions are perfectly sized and the food is so good.
  • Girl and the Goat. Make a reservation as soon as possible! This is one of the hottest places in Chicago. Anything in the West Loop is really delicious though!!
  • Au Cheval. Apparently the best burger in Chicago.
  • Bar Takito. The margarita samplers were more like 3 whole margaritas, not samplers! The food was great too!
  • Mastro’s. It’s not unique to Chicago and pricey but great if you’re celebrating a special occasion! We just celebrated Matt’s birthday here!
  • Mercadito. They have tons of yummy Mexican food. Matt took me here on Valentine’s Day!

wrigley building in chicago

For drinks, there are again tons of options. People love to drink more than they love to eat here! Rooftops are really big in Chicago! Having moved from LA, I don’t see what all the fuss is about but let them love them all the same. Patios are also a big deal as you can imagine! Here are a bunch of great places to grab a drink.

  • Parlor in West Loop. Chill outdoor patio. Also serves great pizza if you want a late night snack.
  • City Winery. You can drink a glass of wine while siting on the river. It’s a relaxed vibe and you can watch all the boats go by. It closes at 9 on Saturdays so it would be great for before dinner or a pre-going out drink. It’s also great for the afternoon too!
  • Federales. A fiesta! Outdoor patio and all the tequila you could want. You can also throw shot glasses against a wall I believe!
  • London House. A little pricy but this hotel is right on the river and is supposed to have some of the best views. It’s right across from the Wrigley building which is one of my favorites!
  • J. Parker. They just redid this swanky spot!
  • Cindy’s. A super cute patio slash rooftop that would also make for a great spot to grab a mid-day glass of rosé after seeing Millenium Park.
  • Celeste. Every one of the 4 floors has a different vibe. The rooftop is so cute!
  • Henry’s. Just a good old fashioned bar with some great dance music. It gets rowdy though so this is for a younger crowd!
  • Godfrey Bar. Haven’t been yet but it comes highly recommended from one of my waitress friends!
  • Gilt Bar. Just a fun spot with a non-pretentious vibe. Lots of character!
  • Signature Room at the John Hancock (see my description above).


bottomless mimosa brunch cruise chicago

Sundays are for brunch! Try any of the places I listed above. If you want a bottomless mimosa brunch on a boat, check out this post for a recap of the one we just did for Matt’s birthday!

chicago architecture tour

My favorite thing to recommend to people is the Chicago Architecture Tour by First Lady Cruises. It’s hands down the best tour I’ve ever taken. You get on a boat and for 90 minutes, get to learn all about the architecture of the city. The Chicago skyline is one of the prettiest in my opinion. I’ve been on this tour 3 times and would do it again so it’s worth every penny (although for a tour, it’s still pretty affordable being under $60 a person). We recommend it to everyone and have yet to hear of anyone saying they didn’t absolutely love it. DO IT!!

Note that these tours take off hourly so don’t be too concerned with buying tickets in advance! There are plenty of options. If you buy on the website, I think they charge you fees but if you buy in person, they don’t. When you’re walking around Saturday, you’ll walk right past the stand (it’s down the stairs on the South East side of where Michigan Ave meets the river). Might want to pick up a few tickets for Sunday then to save your spot! There are also tons of companies that offer these river tours but the First Lady one is the best.

Now you’ve done enough sightseeing and it’s time to relax. Head over to North Avenue to see what Chicagoans call a beach! Disclaimer: California beaches are better. But it is pretty cool to see the skyline while you catch a few rays! Even if you don’t want to tan, the walk along the lake is peaceful and very scenic. If you’ve got comfortable shoes on, walk instead of Uber!

best views of chicago during summer

If you have kids with you or like the zoo, try the Lincoln Park Zoo and Conservatory! We just went two weekends ago and it was just a fun way to spend a day. Stop by Real Good Juice Co. afterward for some vegan froyo (you know I had to throw something healthy in my recommendations).

Depending on when you are heading out, grab dinner at one of the spots I recommended above! Hopefully, by this point you’ve had your fill of carbs, patios, Midwest charm, and some gorgeous architecture!

Now, it’s time to go home after a weekend in Chicago. Hopefully this travel guide helped for my first time visitors to the Windy City!

view of chicago skyline

chicago board of trade building


18 thoughts on “Chicago Travel Guide

  1. Chicago is one of those cities I would love to visit one day! Such great picks!


  2. This is a very helpful post to someone needing some guidance in Chicago! Love it I’ll definitely refer back here if I go visit! Xo

    Jamaria |

  3. What a beautiful city! I love visiting Chicago. The architecture tour is definitely a must! I can’t wait for my next trip back!

  4. I absolutely love Chicago! I haven’t been in about 10 years and I need to go back asap.


  5. Yes!! This is everything I’ve been waiting for! Such a great post. I can’t wait to use this when I plan my trip to Chicago!

Let me know what you think!