First Monday in July we will be in Bucktown/Wicker Park. Want to have Brunch/Lunch somewhere good and that evening a good dinner. We will also consider anything in area (Logan Square or other).
We definitely want to go to Big Star and Violet Hour for drinks, (probably before dinner) want some other recs for after dinner. For Dinner that night or lunch the next day, I was thinking of taking our group to Longman and Eagle or Telegraph at Logan Square.
For breakfast you have to go to Lula Cafe. Get there when they open or you'll be waiting forever. Jam is around the corner and also great if Lula's wait is too long.
Big Star is my favorite place for 'hipster Mexican food'. The service can be spotty and I've waited upwards of 90 minutes for a table but it's still one of my favorite places to go. Have you looked into Revolution Brewery as another dinner alternative?
Longman vs Telegraph: they're two totally different vibes that said they're right around the corner from each other so maybe you could visit both?
There's a restaurant called Birchwood Kitchen that I think is great for an easy, casual lunch. They are BYO and it is counter service (though food is brought to your table), so if you want something more full-service, it may not work. But brunch/lunch options are solid, fresh, creative and very good. I'm not sure what the brunch options would be outside of Saturday/Sunday, so I'd consult their online menu.
Bongo Room is always lively and if you like really sweet brunch options, it's a nice destination, especially on a weekday when the crowds drop off dramatically. Piece is excellent if you like thin-crust pizza and on a weekday, it should be pretty quiet and enjoyable. SmallBar, on Division, has a pretty ambitious 'gastropub-lite' menu, but I doubt you'll find much in the way of brunch options on a weekday. Milk & Honey, also on Division, would probably work well, too.
If you have a group, I'd really look into places that accept reservations. Even on a weeknight, you might find yourself looking at long waits. L&E does not accept reservations and I'm not sure about Telegraph. Lula's offers an amazing Monday night-only prix fixe at $34 for three courses (and no, the entire table does not need to order the prix fixe) and they accept reservations. Down Milwaukee Ave. a little bit, back towards Bucktown/Wicker Park, is The Whistler, another great cocktail destination (no food... also, tiny!).
And I'll second the suggestion for Revolution -- the epitome of unpretentious bar food that's still made with farm fresh ingredients, their beer is among the best in the city. They don't accept reservations, either, and even during a weeknight, you may find yourself looking at a long wait.
To me, one itinerary -- and it really depends on your group size -- would be Whistler - Lula's - Big Star, but there are many, many options.
Lula Cafe and Jam and Longman & Eagle and Telegraph are all very good. They're just not in Bucktown or Wicker Park. They're in Logan Square, which isn't all that far, but a different neighborhood.
For breakfast or brunch in B/WP, I would agree with the Bongo Room. They specialize in very sweet pancakes (too sweet for me) but also have good omelets. Otherwise Both Feast andToast have a very good breakfast and an outdoor patio to eat in.
I would plan on Big Star for lunch and then dinner in the same 'hood at Hot Chocolate or The Bristol or Antico or Ripasso.