Chicago Itinerary: The Ultimate Travel Guide

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So excited to share my Chicago itinerary with you today!

Chicago is one of those cities in the U.S. that I had been wanting to explore for a long time, and people were always surprised that I hadn’t been there yet.

I finally made it out to Chicago for a work trip, and Omied and I extended it into a play trip as well. We ended up visiting during the perfect time of year when the weather was amazing, in early September.

We absolutely loved this city—Omied of course was gaga over the architecture and even I found it to be super interesting to hear about all the famous architects and their stories.

Pssst, heading to Chicago? Don’t miss these travel guides to help you plan your trip!

Where to Stay in Chicago
Chicago 3 Day Itinerary
Day Trips From Chicago
Famous Chicago Food You Have To Try

There’s so much to do, see and eat in Chicago (be sure to purchase a Go City Chicago pass here to save money on top attractions). Here’s how we packed in everything we wanted to hit up in the Windy City.

5 Day Chicago Itinerary

Chicago Itinerary: Day 1

Check-in

We stayed at The Gwen Hotel, which is part of Starwood’s Luxury Collection.

The hotel is absolutely gorgeous, and I adored its art deco vibes. You can see more pics just of The Gwen in this post.

Its central spot on Magnificent Mile means you really can’t beat the location. We were able to walk or take a short uber ride to most places.

In case The Gwen is fully booked, I also recommend the Western River North Hotel located right in downtown Chicago.

Lunch at Cold Storage

We kicked off our foodie tour with lunch at Cold Storage.

This seafood spot had amazing oysters, delicious spreads, and yummy lobster rolls. We finished lunch with a super decadent ice cream sundae, that they are also famous for.

Millennium Park

After lunch, we went over to Millennium Park to walk around.

Millennium Park is famous for all of the incredible, free concerts and events that it hosts, and there happened to be a jazz festival going on when we strolled by.

We also popped over to see The Bean (formally known as Cloud Gate), which was pretty cool but definitely crowded in the afternoon (we came back early in the morning the next day to shoot the above photos).

Cindy’s Rooftop

We hopped just across the street to visit Cindy’s Rooftop, which I’d heard so much about and everyone told me was a must-do in Chicago, even though it’s a tad touristy.

I can see why it’s such an attraction, with its gorgeous views overlooking Millennium Park and fun drinks (terribly slow service, though).

Architecture River Cruise

An Architecture River Cruise is another must-do if it’s your first time in Chicago.

I promise even if your husband isn’t an architect, you’ll still find it interesting. Plus floating down the river gives you an awesome perspective of Chicago’s beautiful buildings.

We booked ours so that we’d be out on the river around sunset, but be sure to book ahead if you’re looking to do the same, as sunset rides fill up fast.

Blue Chicago Jazz Club

Omied and I love to find local spots for live music when we’re traveling, and we had a few recs for jazz clubs.

We popped into Blue Chicago Jazz Club and loved the vibe there—it was so much fun!

Girl and the Goat

After watching Anthony Bourdain’s No Reservations episode in Chicago, I was dying to visit Stephanie Izard’s Girl and the Goat.

She’s the first female winner of Top Chef and has built an empire of noteworthy restaurants in Chicago, with Girl and the Goat being the most popular (and infamously tough to get a reservation, so again, book ahead).

I looooved our dinner here. 10/10 would do again. It’s a super romantic spot and the food was fabulous. Definitely get the green beans, lamb ribs, and ratatouille focaccia with feta and tomato jam.

Ugh, my mouth is watering just thinking about those dishes!

Chicago Itinerary: Day 2

Duck Duck Goat

Back to back Stephanie Izard! Duck Duck Goat is her dim sum restaurant, and we had an incredible brunch here.

Seriously some of the best dumplings I’ve ever put in my mouth. The octopus salad, char sui bao, duck and goat spring roll, crab rangoon were all absolutely to die for.

This was one of my favorite meals of our trip, so I’d highly, highly recommend this place!

Museum of Contemporary Art

The MoCA had an exhibit on Murakami, and Omied and I really like his trippy and weird art so we spent a couple of hours there.

If you’re not into art museums, there’s also the Field Museum and Adler Planetarium to check out.

Petit Margeaux

For an afternoon pick-me-up, we stopped by Petit Margeaux, the cute sister café of Michael Mina’s Margeaux restaurant at the Waldorf Astoria.

We had some insanely delicious snacks, including foie gras (because I can’t say no to foie when I see it on the menu).

The outdoor seating at the café is really cute and pleasant, so it was a nice spot to relax before continuing on with our exploring.

Riverwalk

As the sun was setting we headed back in the direction of our hotel and made our way over to the Riverwalk.

I think it’s so cool that Chicago has a river running through it, and apparently it’s the only city in the U.S. with a river. This area is so beautiful, especially as dusk sets in and all the skyscraper lights turn on.

We sat outside along the river watching the boats go by, and it seemed like the perfect evening.

Until we got caught in a torrential downpour that suddenly started and caught us totally off guard.

Pequod’s

I quickly learned that there are only three acceptable places to get deep-dish pizza in Chicago, and they are Lou Malnati’s, Giordano’s, and Pequod’s.

I also learned that not all three are created equal in each local’s eyes, and everyone has their favorite.

Each Uber driver I had told me I had to go to Giordano’s, the others are terrible. It was pretty funny to see them get all riled up when I told them my previous Uber driver said the opposite, and that I had to go to Giordano’s.

In the end, we decided on Pequod’s, and omg was their deep-dish delicious.

Chicago Itinerary: Day 3

The Highline Bar

I had a coworker who was from Chicago and she used to rave about their Bloody Mary bars. “No one does it like Chicago,” she told me.

“Why doesn’t SF have a Bloody Mary bar with all the fixings? Screw bacon, celery, and cheese cubes. That’s so uncreative.

Think mini sliders, chicken wings, mac and cheese balls. These can all go on your Bloody Mary skewers.

People in the Bay would go ape shit for it!” Clearly, I needed to try one of these fabled Bloody Mary bars, and we found The Highline Bar’s Sunday Bloody Mary brunch to help fill that void in my life.

It was so much fun piling on all the goodies for my Bloody masterpiece (A doughnut? Sure, why not? A bag of flaming hot Cheetos? Hell yes.) and while we left feeling bloated from all the sodium, it was totally worth it.

If you end up loving this spot then you have to explore more of the River North area for great restaurants and bars.

Oak Street Beach

Besides having a river running through the city, I also think it’s super cool that one side of Chicago backs up against the beaches of Lake Michigan.

We went over to Oak Street Beach to watch the volleyball players kill it (and basically be the opposite of us—fat, bloated blobs after Bloody Mary brunch), and to relax on the beach a bit.

Be sure to check out North Avenue Beach too if Oak Street gets too crowded.

London House

After hanging at the beach for the afternoon, we freshened up at the hotel and then walked over to the London House to have drinks at their rooftop bar.

Fair warning, this place draws a crowd that is douchey as hell (too many tight, black v-neck shirts paired with gold chains to count), but the view is pretty awesome.

We watched the sunset from up here and it was worth the long line and other general douchebaggery to get in.

Second City Comedy Show

Everyone told us we had to catch a comedy show in Chicago, and that Second City (where the likes of Tina Fey and Amy Poehler practiced comedy) was the place to do it.

They had several different shows going on and we picked this cast/show, which does a fresh show based on current events (and the bizarre political times we’re living in).

You guys, it was hilarious. Some of the sketches were short and sweet, some required audience participation.

My fav was a cheesy baby-making music song (think the tune of Dick in a Box) about how this guy needed to know if the girl he was on a date with voted for Trump. So good.

Greek Islands

Apparently, the Greek Islands have been around for ~50 years and have been known as THE place to have Greek food in Chicago.

We had a really good meal here, including the flaming cheese, lamb chops, and gyros, but to be honest, I think it may not be as good as it was decades ago since my dad was raving about how insanely delicious it was back in the day, but we left feeling like it was just good.

Chicago Itinerary: Day 4

Lincoln Park Zoo

We spent all afternoon at the Lincoln Park Zoo, which was so much fun. They have so many awesome animals there and I had kinda forgotten how fun it is to go to the zoo!

If you like the zoo, be sure to check out the Shedd Aquarium to see beautiful aquatic animals.

3 Arts Club Café

We had lunch at the uber posh restaurant inside the Restoration Hardware.

This place is an Instagrammers dream, but unfortunately, they asked us to not take photos (you know I still had to sneak one with my phone), because it’s that type of place where they think their clientele is so bougie that they’d be pissed to be captured in a photo.

Be sure to make rezzies in advance, because without it you’re looking at a two-hour wait during the weekend.

Shopping at the Magnificent Mile

You can pretty much shop ’til you drop in Chicago.

The Magnificent Mile is made up of three vertical shopping centers and has basically every store your little heart could desire.

Happy Hour

We knew we wanted to go to Au Cheval for dinner, and that they don’t take reservations, so we put our name in and were greeted with a two and a half hour wait.

That’s ok though, we were prepared and had already scoped out some great bars nearby!

Might I recommend The Allis (in Soho house), RM Champagne Bar, and Bad Hunter next door as great spots to grab cocktails while you wait for your table.

Au Cheval

Okayyyy first of all, yes the wait is worth it, especially since you have so many fun bars nearby to choose from while you wait.

And second of all, if you go to Au Cheval and don’t get their burger, you’re doing it wrong. SO. GOOD.

We also got the bone marrow because we’re fatties. #noregrets

Chicago Itinerary: Day 5

Willis Tower Skydeck

Gotta do the sky deck! Pro tip: when you’re facing the windows with the glass bottoms, you might be tempted to go to one of the shorter lines for the windows on the left, but they are shorter for a reason.

The window on the very right is the one with the best views, so if you’re going to wait in line and get that shot for Insta, you might as well make it worth your while.

It’s definitely a trip to stand on a glass floor 1,450 feet high!

Kayaking on the river

Omied and I love kayaking, and this is another really fun way to see the Chicago river and buildings from a different perspective.

Portillo’s

Clearly, we had to try a Chicago-style hot dog. After trying it, I’m not exactly sure what all the fuss is about, but if you’re going to try a Chicago-style hot dog, I’m told this is THE place to do it.

If you’re not about that hot dog life, I’d also recommend Little Goat Diner. Yes, another Stephanie Izard restaurant.

Clearly, I love this woman’s food. The chicken pot pie and Rueben sandwich were both killers!

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If you are spending more than 5 days in Chicago, I would recommend getting the Chicago Citypass.

You get to visit 7 of Chicago’s best attractions like Shedd Aquarium, Skydeck Chicago, The Art Institute of Chicago, and 360 Chicago Observation Deck in the John Hancock Center Building.

I would also recommend spending some time at Grant Park, the Chicago Cultural Center, Wrigley Field, Chicago Water Tower, and the Navy Pier.

Phew, looking back at our itinerary, that was a lot of things! There’s just so much to do in Chicago, and we had the best time exploring!

I know there are other things (especially restaurants!) that we didn’t get to try so tell me, what else do I need to hit up the next time I’m there?

You can tag me (@wtfab) on insta so I can see where in the world you’re traveling from.

Heading to Chicago? Check out my other Chicago travel guides here.

Where to Stay in Chicago
Chicago 3 Day Itinerary
Gwen Hotel, Chicago
Day Trips From Chicago
Famous Chicago Food You Have To Try
Top 11 Chicago Black-Owned Restaurants
22 Best Indoor Activities Chicago Has to Offer
20 Fun Things to Do in Chicago at Night
18 Most Instagrammable Places in Chicago

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