Chicago Suggestions…?


I just found out I’ll be spending a few days in Chicago following Thanksgiving and I can’t wait to explore. I’ve heard such wonderful things about the Windy City and want to experience the very best. You all were so helpful to my Washington, D.C. jaunt — do you have any tips for Chicago? Restaurants, museums, galleries, boutiques…?! Can’t wait to learn your favorites. xx



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47 comments on “Chicago Suggestions…?

  1. Essie

    You would LOVE the Pump Room in the Public Hotel for a drink. It is absolutely gorgeous. For museums, the Art Institute of Chicago and Field Museum are my favorites.

  2. Shannon

    Chicago is great–I just spent five years living there! Andersonville has fabulous vintage homegoods shopping along Clark St (and the brunch at M. Henry is fabulous). River North has lots of terrific galleries, and they do tours every Saturday morning–you meet at a Starbucks, and someone from one of the galleries takes you around to four different shows. I’d recommend stopping by Xoco (owned by Rick Bayless) for churros or tortas and cafe con chocolat–delicious! The theatre in Chicago is also fabulous–check the Tribune for what they are recommending right now.

  3. Audrey

    The Donut Vault is awesome (go early before the sell out).
    The Art Institute of Chicago is also a must. Prioritize what you want to see ahead of time. It can take days to see everything.
    The Sears/Willis Tower has great views. Try going at sunset.
    Finally, architecture tours through the Chicago Architecture Foundation are fun too. They offer walking, train, bus, and boat tours.
    Have fun!

  4. Beth

    For a little bit of old Chicago get a drink at the bar of Cape Cod Room in ground level of the Drake Hotel- it hasn’t changed much since the 1930’s/40’s and you can still see where Marilyn Monroe and Joe DiMaggio even carved their names into the bar. (Make sure you also go upstairs to see their Christmas decorations)

  5. Meghan

    I grew up outside of Chicago so have many favorites! Milk and Honey and Southport Grocery are my fav brunches and Sweet Mandy B’s for cupcakes of course. Katie, I can email you more just let me know! Have fun! XO


  6. Kathleen

    The Signature Room on the 95th floor of the Hancock Tower is fun for a drink after dinner – they have beautiful views of the city up there. Piece is great for pizza (real pizza, not deep dish!) and craft beer – Brunch at The Bongo Room is excellent and it’s in a cute neighborhood for shopping and strolling afterwards. Bin 36 is nearby and a fun wine bar with tasty small plates. Quartino is a fun wine bar downtown if you’re looking for somewhere to stop in after shopping on Michigan Avenue. And the art museum is really wonderful – one of my favorite museums anywhere. Have fun!

  7. Maggie

    RM champagne salon (for what else?)
    and if it’s not too chilly the fermob luxembourg chairs in the garden at the art institute are a perfect place to rest between galleries.

  8. Erika

    The Green Mill is an absolute MUST. Incredible vintage charm, and every more incredible music. Margie’s Candies is adorable and their ice cream is perfection. I love the antique shops in Edgewater, especially the Broadway Antique Market. Have an amazing time!

  9. Emma

    I second the pump room. Also, Pops for Champagne is a great champagne bar and RM Champagne Salon is also a cute place for a drink. You could get dinner at Maude’s before going to RM. Enjoy your visit and bundle up!

  10. heather

    You must go to the Art Institute of Chicago (one of the most beautiful museums I have ever been in…and I’ve been in a lot), visit the Bean, and peruse the Museum of Contemporary Art. Food wise, deep dish pizza at Lou Malnati’s Pizzeria is a must, as is Chicago Style hot dog at Perillo’s, an Choriqueso Torta at Xoco and dinner at The Girl and The Goat.

  11. Brittany

    Doghnuts at Glazed & Infused are a must! My favorite is The Original, but there’s plenty of options, and even a maple bacon long john option for the gents.

  12. Sara

    You’re going to love Chicago! Some of my favorite restaurants are Nellcote, RM Champagne, Molly’s Cupcakes, RPM Italian, and Mon Ami Gabi. Enjoy!

  13. Katie Erin

    The Library at the Gilt Bar is my favorite cocktails and snacks spot. Lovely decor, charming bartenders, and super drinks (the Gilt Bar itself is also fun, but the Library is more intimate and cozy).

    I also highly recommend the Vincent and Big Jones in Andersonville, Big Star for tacos in Wicker Park, the Purple Pig on Michigan Ave., and GT Fish and Oyster in River North.

    If you can squeeze two art museums into your stay, the Museum of Contemporary art is always great (and free on Tuesdays!).

    Hope you have a wonderful trip!

  14. Kelli Coles

    Enjoy! I was just in Chicago for a conference called Neocon in July for the first time since I was 10 years old (ie it’s been a LONG time)! I enjoyed the architectural boat tour along the river, the views from the Sears/Willis Tower, and the farm-to-table dinner I had at 676 Restaurant at the Omni Hotel. The food was delicious and so healthy, the wine was excellent too!

  15. Rachel

    I agree with the Xoco recommendation–so delicious! Also, I enjoyed Art Smith’s restaurant (hummingbird cake!) & the gnocchi at Spiaggia were to die-for!

  16. Linden

    It’s an hour (or more?) outside of Chicago, but if you have time the Farnsworth House (designed by Mies van der Rohe) is well worth the drive! My husband and I went on a weekday and we were the only people to show up for the tour. The tour guide said we basically got a private tour (which is available, but expensive) for the regular tour price, and she let us wander around for as long as we wanted. It was amazing!

  17. Maureen Sullivan Stemberg, Interiors

    I LOVE Chicago! In the beautiful photo you have of the City skyline … Right by the Water Tower. Is the Park Hyatt. They have one if the best place to dine on the top floor. The food is amazing as are the people. So many great places to eat. Also
    stop at The Ralph Lauren store a great selection of beautiful pieces from all over the world.

    I was fortunate to to work with my design from for a huge developer on The Miracle Mile. Just heavenly… Only problem bring warm clothes and do shop while there…. The prices are so much better than Boston.
    Remember to add to your list The Chicago
    Art Institute! Amazing… Enjoy!

  18. Lauren

    Purple Pig for happy hour, Girl & the Goat, Maude’s Liquor Bar, Big Star for tacos, Violet Hour for drinks, Publican for brunch and the Public Hotel!

  19. cindy wolf

    hi katie!

    i have so many suggestions for you. i lived there for ten years.

    hub51 / river north area / great happy hour place / river north in general happenin place

    boat tour / you MUST do this. the best way to see chicago. i think chicago is architecturally the most beautiful city in our country. you will definitely not be disappointed. i did this at least once a year with friends and family i had visiting and never grew tired. you will get to see the chicago merchandise mart, the largest building in the US and how gorgeous the architecture is winding and weaving through the river. if anything at all, please don’t miss this. i recommend it to all.

    coast / one of the best sushi places in chicago / bucktown nabe / totally hip / it was BYOB, so i’m not sure if it still is. we always brought our own wine.

    shopping on damen in bucktown / every hot boutique known to man

    lunch at fresh choice on wells in old town / not fancy at all but very good, small joint and good to see wells street in old town where lots of movies & shows have filmed etc

    michigan avenue / oak street / material possessions is a store you would love on on wabash old town / these all connect to each other / oak street nicest chi chi street in chicago connection to michigan avenue

    river north area / just a good night life bars and restaurants area

    the art institute of chicago at 111 south michigan / go see the bean sculpture – huge

    frontera grill / on clark / rick bayless chef / not horribly expensive and simply amazing and great part of town

    drinks at the top of the hancock on michigan avenue

    drinks at the penninsula hotel / so grand and cool / lots of chicagoans venture there for happy hour or late night drinks / library like

    see the drake hotel wear princess diana stayed when i lived there corner of oak and michigan, the windiest corner in chicago right on the lake / lake shore drive and oak

    zebra lounge / small dark piano bar / so much fun you have to stop in here where everyone sings together / in the gold coast / down town michigan avenue area

    walk up and down michigan avenue from oak (drake hotel) all the way south to the art institute. you will cover all of michigan avenue and every store. you will love it!!!

    i hope you enjoy!! let me know if you have any other questions. there is so much more. it’s such a great city. happy thanksgiving darling! love your blog.



  20. Allison

    I have to chime in as Chicago is one of my favorites cities to visit! One of my best pals from college lives there and always takes me to the best places to eat. My favorite place for a hot dog is Gene and Jude’s…. voted by Rachael Ray’s magazine to be THE BEST hot dog in America and I completely agree! My friend served them at her wedding as a late night snack. So so good! Not the traditional Chicago hot dog, but delicious! I also recommend Gino’s East for deep dish. I thought I was a NYC pizza gal, but Gino’s East changed my tune! :) Have so much fun! Chicago is the best!

  21. Cathy M

    Definitely take the architectural boat tour! It may be chilly and cold, but totally worth it. Also stop into Giordano’s for a deep dish pizza, and try the local beer – 612. The Art Institute is a must-see as well. Bon voyage!

  22. Tammy Nicastro

    I grew up in Chicago and two of my favorite places when I was in my 20’s that still satisfy me now that I’m in my 40’s and live in San Francisco are NoMI on the 7th floor of the Park Hyatt and North Pond Cafe in Lincoln Park. The Art Institute is a must but like the Met in NY it’s too big to conquer in one day. Jayson Home and Garden on Clybourn is full of beautiful housewares. The architecture along the river and the Gold Coast is worth exploring and of course the Frank Lloyd Wright home and studio in Oak Park is worth the 15 minute drive west of the city. Oak Park has some lovely shops and cafes too. Hope you have a lovely visit!

  23. Emily

    For food & drinks: I would DEFINITELY recommend CH Distillery (in the West Loop) for drinks and food. Also, Avec (West Loop) is excellent! I love Trattoria Number 10 for Italian. The Signature Room, 95th Floor, in the Hancock building is fun for drinks with a great view!

    Also, the Architecture Boat Tour is AWESOME!

  24. Meredith

    Sounds like so much fun! And you don’t have anything to be nervous about – I’m sure you will absolutely charm his family. I don’t have any Chicago tips, but one app for finding great food recommendations is the Find.Eat.Drink app. If you don’t know about it already, it has recommendations from well-known local chefs and bartenders. It’s helped us find our way to some great places in the past!

  25. LL

    Hooray for Chicago! I’m so happy for you to experience the windy city!

    Longman and Eagle: One of my favorite restaurants anywhere. I’m honestly shocked that there aren’t a million suggestions for this place! Every time I’m back in Chicago, a long, boozy dinner here is a must.

    The Art Institute of Chicago: To second a previous commenter, one of the most beautiful museums I’ve been to. If you’re strapped for time, this is the one to visit!

    The Drake Hotel: This one is obvious.

    Girl and the Goat: Amazing, but normally requires reservations months in advance! If you find an opening, take it!

    It’s hard to go wrong with brunch! Chicago takes it pretty seriously. There are so many incredible options: The Bongo Room (um… Chocolate Tower French Toast?), Milk & Honey, Floriole (for baked goods), Toast…

    I can’t wait to see where you two end up. Have the best time!

  26. Kathryn

    Dinner and drinks in the West Loop! I suggest Vera, Maude’s, or Little Goat! Wander around the Gold Coast. A walk by the lake (though it will be windy!). A show at Second City.

  27. Emily

    Definitely try to get a doughnut from Glazed & Infused. Also, the Southern is great for cocktails! The Art Institute also has a great exhibit called ‘Art & Appetite’ right now!

  28. danielle

    ooh! you must go to POSH Chicago on state and chicago (chicago or grand) adorable french flea market finds! they have a gigantic selection of vintage bar ware and kitchen accessories! you should also get a cappuccino + croissant from floriole bakery in lincoln park, so delectable! xx

  29. Allison R.

    Hey, Katie! Glad you’re coming to visit us in Chicago! Here are some places you may enjoy:
    Una Mae’s (Wicker Park) – for some good winter staples and maybe something for the boy
    Fleur (Logan Square) – beautiful flowers, planters and home goods
    Sprout Home Chicago (Ukranian Village) – teaches a wonderful terrarium-making class
    Field Museum (South Loop) – their Wonders of the 1893 World’s Fair exhibition just opened
    The Music Box Theatre (Lakeview) – celebrating their 30th anniversary while you’re in town
    Floriole (Lincoln Park) – award-winning bakery that sells beautiful French pastries
    Lula Cafe (Logan Square) – for consciously sourced, thoughtfully prepared meals
    Longman and Eagle (Logan Square) – whiskey, flannel and an amazing inn upstairs

    Safe travels!

  30. Sabrina

    You should have dinner or drinks (or both!) at the Signature Room. Its located on the 95th floor of the John Hancock building and has great views of the city!

  31. Hannah B

    Our favorite city! There is some amazing vintage shopping to be found, & the food is amazing! (Our fav is Yoshi’s in Boys Town.) But, if you can catch them, the Chicago Symphony will blow your mind & bless your heart. Safe travels!

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