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Two day Chicago visit in May

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My husband and I will be visiting Chicago next week for 2 days only May 4th and 5th. We will be staying at the Peninsula on the Magnificent Mile. It's actually a business trip for him and I'm just flying in Friday to meet him. We're looking for recommendations for dinner Friday night, Saturday brunch and dinner Saturday night. Also, maybe a cool spot for drinks Saturday night before dinner and if anyone has ideas about places to hear good music that would be great (I know that's not the focus here but we do love our music). We are thinking pizza Friday night at Uno or Due. Saturday brunch we are trying to decide between North Pond Cafe in Lincoln Park or the Publican. I want to do some shopping and I've heard Lincoln Park is a good place. I'm interested more in small boutique shops rather than big chain stores. Saturday is Cinco de Mayo and I would love to go to Frontera Grill. Would it be possible to get in? If not, any other recommendations would be appreciated. The Aviary sounds like a cool spot for drinks. By the way, we have never been to Chicago and I have no idea if any of these places are close to where we are staying but we can always take a cab. To sum it up, we like good food, good drink and good music all with fun lively atmospheres.

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  1. There is a world of difference between North Pond and The Publican.

    North Pond is located in Lincoln Park (the park for which the neighborhood was named) on a skating pond. The restaurant, itself is in an Arts and Crafts warming room for skaters on the pond. it is quiet, romantic refined and the food is sometimes excellent and sometimes less good, altho the chef is the recipient of several James Beard awards. Their brunch is no big deal foodwise and they only do brunch on Sunday.

    Publican is a gastro pub. The food is daring and delicious. It is fun and it can be boisterous. You can be seated at a communal table (make the request for a private table when you make your reservations. It has an extraordinary offering of beers and ale from around the world. You mentioned lively atmosphere- this is the spot for it.

    Check opentable.com to see if you can get a reservation for Frontera. If not, you could get there when the restaurant opens, wait for seat at the bar, and dine from both the Frontera menu or the Topolobambo menu. Alternately, I would recommend Mexique, a regional Mexican restaurant with a French accent (love their "French" onion/poblano pepper soup).

    For shopping at small boutiques, I would go to Wicker Park/Bucktown rather than Lincoln Park. Both are a cab ride away. You could stop for lunch at Big Star and enjoy extraordinary tacos, a good beer or margarita and the fun crowd. Also in that area you might look into Hot Chocolate for lunch, dinner or dessert or The Bristol, another of my personal favorite gastro pubs.

    3 Replies
    1. re: chicgail

      Thank you so much for the info! I think we're going with brunch at the Publican on Saturday and maybe Mexique for dinner if we decide against waiting at Frontera. There are so many restaurants that sound wonderful in Chicago it's almost overwhelming. Next time I will plan ahead!

      1. re: chicgail

        One more thing......... Am I wasting my Friday night Chicago culinary experience by eating at Uno or Due?

        1. re: jonas1

          No! They are Chicago institutions. Uno created Chicago Style Deep Dish pizza in the 1940s and, after they created the demand, opened Due. There is a (horrendous) chain out there that uses the same name and even markets a frozen pizza. They chain does not use the same recipe and there is no comparison.

          Now, that being said, if there is something else that calls to you, I would urge you to explore it. You might want to look on opentable.com to see what is available for that Friday night. We would be happy to respond to any questions you may have about anything you find available on that site.

      2. would agree on Publican over North Pond for brunch.
        On Frontera- I don't think they do reservations on open table (only Topo does)- you have to call the restaurant to see if they have any reserv avail, but it's worth a shot.
        Lastly on your question for fun cocktails- may depend on where you're having dinner and if you are looking for a destination cocktail place or just somewhere to stop that's nearby where you are having dinner. For destination cocktails- I would say Aviary, Violet Hour, and the Drawing Room. Another good spot in River North is Sable.