In my 20s I would forget about the food and my nights out were all about drinking.  Back then I was a lager or cider and blackcurrant girl.  The food would be perhaps chips from the local Chippy (in England) on the way home after the pub or a bacon buttie (sandwich) in the morning, which got me over any hangover lickety split. 

In my 30s as long as I had a bite to eat before leaving the house for cocktails, I was good to go.  My drink of choice was always a vodka tonic with extra lime.  A hangover would last until late morning and usually with a “I will never do that again!” comment.

In my 40s it’s all about the perfect balance of good food and wine, which I manage almost to perfection these days and on this Chicago trip I accomplished just that.  Hangovers last far too long and are totally not worth it – not that I haven’t slipped up a few times here and there.

Here is my great (I think) itinerary, which I was of course in charge of, for the perfect Chicago weekend that embodied everything we (me and my friend, Jen) 40-something girls wanted to do…  Food, Wine, Sightseeing and Shopping.  I would also say this is also an itinerary for any age.

SATURDAY

No reserved plans for lunch as I wanted both of us to get checked in and have a little walk around, we had the whole day ahead of us.  We found a fun restaurant called Howells & Hood right near our downtown hotel.  This place is enormous inside and out. 

What to order?  Without question the Butterbean Hummus – awesome share dish.

Why go? Well, it’s fun, has a lovely outside seating patio and friendly, very accommodating waitstaff.  They also have 100s of beers on tap and are only too happy to explain to beer neophytes like me what I would like based on my tastes. 

What to check out:  Cloud GateThe Bean” at Millennium Park.  Really fun for photos.  People watching at Navy Pier.The rest of the day involved walking through Millennium Park, photos at the bean and over to the Food Festival.  Then we jumped on a bus and popped over to the crazy busy, but amazing people watching Navy Pier for ice cream.

Why go:  The Pier is great for kids if you have them.  For myself and Jen it was just ice-cream.

What to order:  One of my already featured Fab Dish Fridays, the Sunnyside Up Organic Egg Fork & Knife Pizza.  Dinner plans was at the highly recommended, uber trendy and most “in” restaurant in Chicago, called Nellcôte in the Randolph Street Corridor.  At least that is what we were told and to be honest that is what we got.  This is a truly trendy establishment.  Cool vibe, great space and good food. 

Why go:  If you want to be part of the in-crowd this is where you need to be for dinner.  Ask to be seated at the balcony, which overlooks the restaurant.

We had heard about another cool place called RM Champagne Salon so we asked for directions from our waiter.  Surprisingly, it was connected to Nellcôte so we were escorted through the kitchens to the dark and sultry bar at RM.  I almost didn’t feel cool enough to be in this space, but soon got used to the easygoing nature of the mid-westerners and very quickly felt at home.  This place is COOL!  If I lived in Chicago I could imagine being a regular.

What to order:  Of course champagne but also The Dessert Sampler.  Bite sized sweet delights.  I can say with certainty the following are very desirable… Chocolate Macaron, American Gateau, Hazelnut Truffle and Vanilla Bouchon. 

Why go:  This is where the cool kids go!

I had done my research on brunch, my favorite meal, and found a place called Big Jones, which was voted best Chicago brunch many times over by numerous sources.  Southern cooking with unique flair and love.  Located in the lovely little neighborhood of Andersonville, about 7 miles from downtown and worth the taxi ride. 

SUNDAY

Why go:  Mid-western and southern charm rolled nicely into a long, lazy and extremely tasty brunch… with beignets.

What to order:  Everything we had was good, however, no need to order these as they just arrive at your table… beignets.  As good as Café du Monde and free!

After brunch we walked around the cute Andersonville streets for a while until it became too hot so popped into a store called Andersonville Galleria, which features around 90 local artists, designers of jewelry, clothing, artwork, gifts and lots more.  We were in there for ages and walked out with a new leather bag each and a bracelet for me.  A worthwhile trip.

What to buy:  There is so much you will not be able to help yourself with making at least once purchase.

Why go:  They support local artists and designers and they offer really nice stuff.

Later in the afternoon we did one of my favorite Chicago attractions, the Architectural Boat Tour.  A 90 minute leisurely tour down the river to explore the rich history of Chicago’s unique and diverse architecture.  This is not boring for one single moment.  Our guide was so knowledgeable and full of stories I was engaged the whole time.  

When to go:  When it is not raining.

Why go:  You will feel you have done something cultural during your trip and you will get an education along the way.

I realized as I am typing this was an insanely busy day for a vacation.  Woops sorry Jen :).

Dinner on Sunday evening was at the very well-known Café Ba-Ba-Reeba in Lincoln Square.  A warm, welcoming and friendly tapas restaurant designed perfectly for huge parties, families, date nights and girls on a night out. 

Why go:  This is a great place to unwind, try lots of tastes of food and Sangria.  I feels like you are in a traditional Spanish restaurant in Spain!  Paella is also very good.What to order:  The Sangria – fantastic!!! 

MONDAY

Monday was a little more relaxed with another walk to Millennium Park but this time to meet a Chicago (work) friend for lunch at the Park Grill.  The inside restaurant feels a lot more formal for dining than the huge outside patio, which is where I enjoyed lunch last year.  A nice space but a bit more power lunch crowd than tourist crowd.

What to order:  If you have overstuffed yourself on the weekend, the salads are great, however, we all raved about the Wild Mushroom Flatbread with truffled ricotta. 

Why go:  If you are in Chicago for fun, I would recommend the outside patio of the Park Grill.  Last year we were given free Cubs tickets from the bartender four rows back from the dugout!

Our Monday ended with a visit to The Art Institute of ChicagoI absolutely love walking the halls of this beautiful museum.  They have eight-buildings, which if you truly want to explore and enjoy each building, you may need a few days.  We walked the halls quite quickly and focused on what was important to us.  For me the new exhibit featuring Expressionism, Fashion and Modernity was worthy of hanging out for a bit.

What to focus on:  Whatever your heart and interests desire.  Personally for me and it couldn’t be more diverse, I love the impressionists and anything to do with Egypt.

Why go:  It is just an amazing museum with something for everyone and also adds to the cultural palate one sometimes needs to feel more rounded.

So, I am exhausted, how about you? 

What is your favorite city to visit?

Tracey

RM Champagne Salon Menu, Reviews, Photos, Location and Info - Zomato