Itineraries

Chicago

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There are not words for how amazing my trip to Chicago was last week. I’m not the world’s best traveler; however, this trip really left me feeling energized and happy (instead of drained and tired). My feet were certainly sore, but my heart was as full as could be.
When booking the trip, I tacked on a few extra days for my meet and greet because I found such a great price for flights. I was hoping Garrett’s schedule would allow him to travel, but he couldn’t get away, understandably.
This was also a little bit of a different trip for me. I didn’t pack my days with minute by minute agendas or try to squeeze in outfit shoots. Instead, I made time for friends and Garrett’s family, meeting with a few brands based out of Chicago, and plenty of time for wandering around. 
Chicago is my favorite city. It’s so walkable, everyone is ridiculously nice (the rumors are true), and it feels so much cleaner than what you’d expect.
I just missed the peak of the tulips, but still managed to find some great ones around town.
I also think I should note that I really lucked out with the weather. It was gorgeous. I think Chicago was showing off for me and putting on its best behavior.
I had lunch with my friend Liz at the Ralph Lauren restaurant. It was incredibly cute, and the food was fantastic. I wanted to go back again and sadly didn’t have the chance. 
After seeing 3 Arts Cafe in the Restoration Hardware all over Instagram for months, I was dying to go. I ended up having a meeting there for breakfast on Thursday and then drinks at night with a friend on Saturday. It. Is. Awesome. 
I also had lunch one afternoon with Jess and Hallie at The Hampton Social. The decor here is everything navy and nautical!! We had so much catching up to do that we sat there for hours chatting and eating too many French fries.
I prioritized time with friends and family over being a tourist, but I still made some time to see a few things. The Art Institute of Chicago was at the top of my list, and it’s open until 8 pm, which helped a lot with scheduling! I’m no art history buff, but walking around and reading as much as I can about the artwork is my favorite. This time around, I went straight for my favorites.
One thing that I did this trip that I’ve never done before: switch hotels last minute. I realized that where I was staying wasn’t in the best location. I found a great, last minute deal at the Loews Hotel. It was the best decision even if it was a little out of character. It made getting around so much easier and, not going to lie, the room service part was a favorite. 
See what I mean by beautiful weather???? 
And, of course, the reason why I was there in the first place… the meet and greet at Vineyard Vines. Meeting readers is one of the highlights of blogging. It puts everything into perspective, and it’s always nice to put actual faces to avatars and handles!
Garrett’s brother and sister live in Chicago, and it was fun to get to see them (and his brother in law and sister in law and niece!). I went to his sister’s condo one afternoon, and we sat outside soaking up the sun and taking in the downtown skyline. How great is that panoramic view? 
There was still a lot on my “want to do” list, so I think I’m going to have to make another trip out there. 


xoxo
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21 Comments

Laura Cronin

I used to go to Chicago every year for work training and it really is a great city. I especially like shopping on the magnificent mile and seeing the amazing stand-up comedy shows at the improv theaters! Sounds like you had a great trip and lucked out with the weather!

Laura | Laura Aime Vous

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Sarah Edwards

You definitely had the best weather we've had in a while! I was bummed I couldn't make it to VV on Sat., but glad you had a great time! 3 RH is unreal 🙂

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Jordan A

I'm glad you enjoyed your trip! The weather was totally showing off for you, it was freezing at the beginning of the week! It was so cool to meet you, I hope you and Garrett come back soon!

Jordan @ NorthShoreProper.com

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Allie

Chicago is such an amazing city. I was able to go a few summers ago to visit a friend out there and couldn't believe how clean and welcome it is. Hoping to get back, but loved reliving it through your pictures!

Allie, http://www.coralseahorse.com

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Kaitlin Olivero

The city definitely was showing off for you! So sad I couldn't make it to the Meet and Greet, but deff come back! And you can certainly play tourist at Shedd with me 😉

Loved all these photos!!

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A Fishman

Oooh looks like you had so much fun! I literally sprinted by the Vineyards store while you were there because a work thing came up but hopefully next time you're in town you'll do another meet and greet! ALSO SO EXCITED YOU WENT TO 3 ARTS! That place is a total photographer's dream 🙂

Hope to see you in Chicago again soon!

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TCP

Chicago!

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Remember when I did that reader survey to vote for my next meet and greet city?! I was blown away by the thousands and thousands entries. It was also amazing to see how far and wide TCP readership is. It made me so happy to see.
Chicago was one of the top three cities! A few things all fell into place within a couple of days of each other (including a $20 Jetblue flight?! amazing!) and we finalized the plans for the meet and greet!
Mark your calendars for May 21st at the Vineyard Vines in Chicago. I’ll be sharing more details soon but I wanted to make sure you could schedule it. 
I’m actually going to be spending a few full days in Chicago and I absolutely cannot wait. I’ve been a few times, but my last trip was the summer after I graduated high school. So I’d love your recommendations for restaurants, shops, cafes, hotels, photo op spots, things to do, people to see!
I dug through old photo albums on my computer for these. Above is a photo from a freshman year chorus trip. Below is a photo from a sophomore year journalism trip. And the last photo is from a family trip after I graduated high school. I’ve loved it every single time I’ve visited so I’m quite excited to visit as an adult. It’s always been one of my favorite cities. 
Hope I get to meet you on May 21st!!!


xoxo
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21 Comments

Sam Spellman

You come to the midwest just as I head to the east coast for the summer… Hope you have an amazing time!! Love grabbing the train for a day in Chicago.

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Kristina

Lol I had that same green peacoat back in the day! One of my favorite places in Chicago is the west loop neighborhood, it has SO many good restaurants. Lincoln Park (on Armitage and Halsted streets) is full of cute boutiques and restaurants too.

Kristina does the Internets

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Amanda Gehring

Au Cheval – in the West Loop, small and usually a long wait, but it's widely recognized as the best burger in Chicago. There's a bar next door called Lone Wolf with cute couches as booths that would be great to grab drinks while you wait
2. Little Goat Diner – upscale diner with delicious coffee by Chef Stephanie Izard from Top Chef
3. Big Star – THE BEST tacos and margaritas with the cutest outdoor patio space
4. Bar Siena
5. Cindy's at Chicago Athletic Club – amazing view and great for cocktails with friends
6. If you're looking for a splurge dinner, RPM Italian or RPM Steak are fantastic and owned by Giuliana and Bill Rancic. I'd suggest making a reservation a few weeks in advance though to guarantee a spot.

Hotels in River North, Gold Coast, or Lincoln Park are great because they tend to have great city and/or lake views.

The 606 just opened (similar to the High Line in NYC), so if the weather is nice it's worth checking out. The bean in Millennium Park and Maggie Daley Park are great outdoor spots. If you fly into or out of O'Hare airport, there's a new Fashion Outlets of Chicago mall there that is PHENOMENAL, so I'd recommend a shopping trip for sure. Wicker Park has some great boutiques and record stores and tons of great restaurants with amazing rooftop spaces.

So excited to finally be able to meet my favorite blogger!

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alaina shea

I can't wait to meet you!! I have loved being in Chicago for my four years of college and here are some of my recommendations!

Tesori (Loop) has great Italian food and drinks and is a perfect price point.
RM Champagne (West Loop) is great to grab a glass of champagne, and has cute lights in their alley tables during the summer.
Strolling Lincoln Park shops and cafes is a great way to spend a nice day.
Piece Pizza (Wicker Park) is delicious (as well as Pizanos in the Loop)
Kanela in Lakeview is the best spot for brunch!
Vivo (great Italian), Parlor Pizza Bar (awesome atmosphere and roof top) and Hello Taco (best tacos, cute place) are my favorites in the West Loop!

Of course there are the classic places like the Bean and such, but I highly recommend just picking a fun neighborhood (Lincoln Park, Wicker Park, Lakeview, Pilsen, West Loop, and River North are the best) and walking around and exploring – that's the best way to enjoy Chicago!

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Evelina Snell

If you're looking for the best fried chicken in Chicago, make the trip to The Roost Carolina Kitchen on Irving Park Rd! Lincoln Park Zoo, the lakefront – a lovely walk, and if there's a Cubs game – get tickets!!!

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Jessica

Chicago is my favorite 🙂 Sweet Mandy B's in Lincoln Park is darling and their sprinkled sugar cookie is the best I've ever had! Home Slice is a really fun pizza spot with a great patio and a walk along the lake shore has never disappointed me. Have a great time!

26 and Not Counting

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Haley

So excited you're coming to Chicago – I'm flying back from abroad that day so hopefully I'll be able to make it! Go to Ed Debevic's for a fun 50s diner experience, get deep dish pizza at either Lou Malnati's or Giordano's, go to The Hampton Social for their cute Rosé wall for an Instagram pic (and the food is great too!). Also go to the 95th floor of the Hancock building for a drink to see amazing views of the city!!

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Megan Bos

Ah so excited you're coming to Chicago- so bummed I won't be in town that day!

Just as others above I recommend exploring a neighborhood outside of the magnificent mile! They are all great, but each have their own feel.

I recommend making reservations at restaurants you're interested in going too asap – some of the places fill up quick!

Here are some of my go-to activities-

Take a walk or Rent a blue Divy bike enjoy the awesome lakeside path that runs north and south! If you start down town – ride up to the Lincoln Park Zoo, if you start North, ride down to Millennium park.

The Chicago architecture tour is fantastic, if you want to do one super touristy thing I recommend this – you get to be on the Chicago River and enjoy learning about the awesome history.

Since you'll be here in the summer on Saturday evenings there are fireworks at Navy Pier to enjoy. Check out what is happening in the city that weekend – Millennium park often has free concerts or shows, grab snacks for a picnic at Eatly and see a show in the park.

For a great view grab a drink at the J. Parker or in the 360 lounge. For a great meal (in addition to all the awesome places listed above) Celeste (Obama's fave fried chicken in the city, speakeasy feel), Mon ami gabi (French), Mindy's Hot Chocolate (dinner and dessert), Summer House Santa Monica (great lighting and perfect for lunch), The hampton social (east coast feel in the city), The happy camper (great pizza bar), Blue Door Farm Stand (best for lunch), Cafe Babareba (spanish, tapass).

Chicago is well known for their doughnut scene, everyone has their favorites but ones to consider Stan's (my fave), Doughnut Vault, Glazed and Infused, and Firecakes.

Chicago is all about the food and the lake life – so enjoy both when you're here!

Hope you have an awesome time!

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Lauren

I am SO excited that you will be in Chicago! You're coming at a really awesome time….and if you've never flown Jet Blue before, it's really quite nice!
Some things I'd recommend in Chicago:
1. Lincoln Park is definitely an awesome neighborhood to spend some time. Shopping on Armitage Ave is fantastic as well as walking down to the actual Lincoln Park and harbor that is right there. The Lincoln Park Zoo is a free zoo with amazing views of downtown. And the animals there are extremely active (I've heard the male lion roar 2 time there!). There are also some awesome restaurants in Lincoln Park as well. Barcocina: awesome for outdoor eating if its nice, margaritas and tacos. And Cafe BaBaReba: AMAZING tapas restaurant!
2. If you are going to spend time in the Loop or Stay there, I highly recommend River North and the Gold Coast. Quartino is an italian style tapas restaurant in River North that is amazing. Oak Street has the best shopping: the CUTEST Kate Spade boutique, Tory Burch, etc. Rush Street (which intersects with Oak Street) also has amazing shopping and some really nice restaurants including Hugo's Frog Bar and Gibson's Steak House.

Some toursity things I would avoide: The Sears Tower (Willis Tower) skydeck. The views from the Signature Room on the 95th floor of the John Hancock Building are SOOOO much better! And you can grab a cocktail up there. Also-Navy Pier. I would only go to Navy Pier if you're interested in eating at a classic "Chicago" restaurant (Bubba Gump Shrimp restaurant from Forrest Gump, or Harry Carry's restaurant, or Billy Goat Tavern). There isn't much else to do at Navy Pier.

I Would HIGHLY recommend some of the Chicago Museums. The Art Institute (right on Michigan Ave next to Millennium Park) is having an AMAZING Van Gogh exhibit that will still be there. It was voted one of the best art museums in the world! In the South Loop, are all the other museums The Shedd Aquarium, the Adler Planatarium (check out their website-they have "Adler After Dark" which is cocktails, music, and start gazing), and the Field Museum–which has the only fully constructed T-Rew (Sue) skeleton in the world!

Chicago is a pretty awesome city! Have so much fun! I can't wait to meet you!

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Lauren

I am SO excited that you will be in Chicago! You're coming at a really awesome time….and if you've never flown Jet Blue before, it's really quite nice!
Some things I'd recommend in Chicago:
1. Lincoln Park is definitely an awesome neighborhood to spend some time. Shopping on Armitage Ave is fantastic as well as walking down to the actual Lincoln Park and harbor that is right there. The Lincoln Park Zoo is a free zoo with amazing views of downtown. And the animals there are extremely active (I've heard the male lion roar 2 time there!). There are also some awesome restaurants in Lincoln Park as well. Barcocina: awesome for outdoor eating if its nice, margaritas and tacos. And Cafe BaBaReba: AMAZING tapas restaurant!
2. If you are going to spend time in the Loop or Stay there, I highly recommend River North and the Gold Coast. Quartino is an italian style tapas restaurant in River North that is amazing. Oak Street has the best shopping: the CUTEST Kate Spade boutique, Tory Burch, etc. Rush Street (which intersects with Oak Street) also has amazing shopping and some really nice restaurants including Hugo's Frog Bar and Gibson's Steak House.

Some toursity things I would avoide: The Sears Tower (Willis Tower) skydeck. The views from the Signature Room on the 95th floor of the John Hancock Building are SOOOO much better! And you can grab a cocktail up there. Also-Navy Pier. I would only go to Navy Pier if you're interested in eating at a classic "Chicago" restaurant (Bubba Gump Shrimp restaurant from Forrest Gump, or Harry Carry's restaurant, or Billy Goat Tavern). There isn't much else to do at Navy Pier.

I Would HIGHLY recommend some of the Chicago Museums. The Art Institute (right on Michigan Ave next to Millennium Park) is having an AMAZING Van Gogh exhibit that will still be there. It was voted one of the best art museums in the world! In the South Loop, are all the other museums The Shedd Aquarium, the Adler Planatarium (check out their website-they have "Adler After Dark" which is cocktails, music, and start gazing), and the Field Museum–which has the only fully constructed T-Rew (Sue) skeleton in the world!

Chicago is a pretty awesome city! Have so much fun! I can't wait to meet you!

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A Fishman

Woop woop, so excited like a few others that you're coming to one of the best cities in the world!

Just wanted to correct one thing though: the Van Gogh exhibit actually closes May 10th, so it won't be available when you visit 🙁

If you want a place to drink and take beautiful photos: Three Arts Club at 1300 N Dearborn St – great architecture.

If you want to rent a Divvy, definitely go for a ride along the Lakeshore. Trail goes from Museum Campus (south) all the way up North to Wrigleyville. There's a few beaches along the way — Oak Street Beach has some cool graffiti around it. Just keep in mind Divvy's only last for 30 minute rides. There's also a brand new river walk in the heart of the city that's supposed to be amazing once it's actually warm out!

If you like fusion food, I highly highly recommend Sunda (110 W Illinois St) – it's Pan-Asian, sushi, and amazing drinks.

Something more hole-in-the-wall, go to Crisp up north on Broadway St – Korean/American BBQ fusion. They have amazing veggie bowls!

Breakfast – The Girl and the Goat in West Loop.

Burgers – Au Cheval is AMAZINGGG but wait times are crazy so get there as early as possible (be prepared to wait 1-2hrs).

Also picturesque: The parks in the loops. There's Millenium (with Crown Fountains and Lurie Garden), Grant, Maggie Daly, and then further south is Northerly Island.

And lastly, pizza. Due/Unos/Gino's East/Piquod's/Pizza Oven and Grinder Co (on Clark St).

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A Fishman

As for shopping – Michigan Ave (north of the river) has high-end shopping. State St in the Loop (south of the river, by Millenium Park) has more stuff like Urban Outfitters, Nordstrom Rack, H&M, Zara, etc.

If you love cars, literally just walk around my neighborhood (Gold Coast). I live above an Aston Martin dealership (I die every day I walk by it), and there are so pretty cool Bentley/Rolls/Ferraris always parked around Rush and Chestnut/Chicago St.

Water Tower is a pretty typical mall – more or less what's on Michigan. They do have a tiny little Lush store in there though!

Around Vineyard Vines is a Madewell, LuLu Lemon, Ugg, Frye, etc. If you get to the Rush/State/Bellevue triangle there's a few restaurants around there like the famous Gibson's Steakhouse, Hugo Frog's, Tavern on Rush, and Carmine's!

Also seconding the architecture boat tours. It'll be the perfect time to go because it's not going to be cold or as windy.

That was a lot, but this city is amazing. No matter you do you can't go wrong. Can't wait to meet you, and I hope you have a wonderful time if I don't get the chance to!

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Heidi

So excited for you to experience Chicago! I grew up three hours south of the city in the middle of nowhere, so whenever we needed a "big city" fix, we'd drive up and spend the day or weekend there.

Velvet Taco is one of my favorite restaurants in the city. You have to try their tater tots–truly potato heaven. Tots and tacos might sound like a weird combination, but it totally works! I also love Glaze Teriyaki for some great Asian food, and Yolk or Girl and the Goat for brunch is a must!

Enjoy your stay in the Windy City! It truly is magical.

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Brittany

Excited to come see you in Chicago! I haven't lived here long and am enjoying everyone's recommendations as well. Cross my fingers I'm not scheduled to work that day.

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Chrystina Noel

What a fun idea! Chicago is on my list this year, I can't believe it's taken me so long to get there. Also, if Philadelphia is on your list, let me know. I've got a guest room with your name on it if you're interested. Or you can just crash.

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