The history of Chicago is rich and storied. The city started as a gateway to the Mississippi River basin. From Lake Michigan, ships brought goods that supplied the midwest and blah blah blah Great Fire of 1871, immigration, deep dish pizza, Chicago dogs, Chicago Cubs, Al Capone, Art Deco, Prohibition, speakeasies, Mayor Daley, State Street, South Side, the Magnificent Mile, and the Sears tower (we mean the Willis Tower). Honestly, there is way too much history and diversity for a single paragraph. It’s Chicago for crying out loud, not __________ (insert small and culture-less city of your choice here).
No other city in the country resembles New York more closely than Chicago. Let’s take a look at some of the similarities: proximity to massive water body, check. Large downtown financial district, check. Melting pot of ethnic diversity, check. Chic shopping and cultural districts, check. Incredible, growing food and party scene, massive check. It’s easy to see why Chicago was our kind of town.
Chicago is a quick 2 hour flight from NYC. Need even more incentive to take the trip? The roundtrip flight costs around $200 and if you carry on there are no luggage fees. How come we have never been here before? Well, that all ended quickly when L said he was heading there for a business trip. After some quick discussions, it was decided that the entire crew would turn it into an event.
L arrived on a Tuesday afternoon in full business mode thinking ABC (Always Be Closing) and “Coffee is for Closers” (Do we need to explain the Glen Garry Glen Ross reference here?). Okay, he was really there to learn some scientific things with other environmental dorks from around the country. Business deals were secondary. What a nerd…
The first three days of the trip were filled with listening, talking, and learning at the Palmer House Hilton located in the center of The Loop/Theater District and just steps from the Art Institute and Millennium Park. The 140-year-old historic hotel (all of the big music acts have played here….think Sinatra) has a beautiful hotel lobby including a massive frescoed ceiling. Morning runs down the Magnificent Mile and Millennium Park and an unforgettable meal at Gene and Georgetti’s were the highlights of the first few days.
When A arrived on Thursday, L was ready for a break and change of scenery. Since The Loop is sleepy at night we switched to the James Hotel, which is on the Northern end of the Magnificent Mile. This contemporary boutique hotel has well-appointed rooms, a great lobby bar, David Burke Restaurant, and a hotel-owned lounge next door for late night drinks. It was a perfect backdrop for the remainder of the weekend.
On Friday, as L finished up his work responsibilities A strolled the Magnificent Mile, shopping at Chanel, Gucci, Tory, Louis… L caught up with her just in time to slow the buying frenzy and tempt her with some deep dish pizza. Later that night K and M arrived at the hotel, hungry and ready to party. Our late night dinner at The Girl and the Goat hit the spot. Exhausted after closing the place down and practically getting kicked out, we called it a night.
The next morning in search of breakfast we hit the Navy Pier. This was a bad idea. Hungover and exhausted from the night before, the screaming kids and stagnant air inside the Navy Pier were unbearable. We hopped in a taxi, walked through Millennium Park taking in the “Bean,” amphitheater, and Art Institute of Chicago. Thankfully, we stumbled upon The Gage, a contemporary Irish restaurant with an incredible brunch. The morning was saved. We walked back up State Street taking in all the sights and making a few stops. That night we had life-changing bone marrow at Maude’s Liquor Bar.
The dreary Sunday morning was instantly brightened when we arrived at Wrigley Field for a behind the scenes tour complete with a visit to the locker room and dugout of the historic stadium. The weather broke just long enough during the afternoon for a quick visit to the top of the John Hancock building for cocktails. What an incredible view. After a superb lunch at the Purple Pig and with time running out on our little trip, we rushed to Buddy Guy’s Jazz Club for an hour of matinée jazz. We ran out of the club, hopped in a cab, grabbed our bags and hit the airport just in time for our flight back to New York. Exhausted.
Mostly work, a little play: Tuesday-Thursday
As a complete Chicago novice, the size of the city is impressive. Though most of the first few days were filled with with listening, talking and learning, there were some highlights. First, the Palmer House Hilton located in the center of The Loop/Theater District and just steps from the Art Institute and Millennium Park was quite impressive. The 140-year-old historic hotel (all of the big music acts have played here…think Sinatra) has a beautiful hotel lobby including a massive frescoed ceiling. Most of the down time during the conference was spent hanging out in the lobby reading the paper and people watching.
Chicago is semi-sleepy in the morning. It is one of the huge differences between it and New York. However, morning runs down the Magnificent Mile and Millennium Park just after sunrise provided some of the best sightseeing of the trip. Unfortunately, frequent stops at the major sights to take pictures made the morning runs more sightseeing and less cardio.
There were a few meals over the first three nights but none better than the one at Gene and Georgetti’s. Founded in 1941 and located in the River North, Gene & Georgetti is Chicago’s oldest steakhouse. Seventy-one years of experience aside, Gene and Georgetti is the best steakhouse L has ever eaten at hands down. Everything was first class from the service to the food. L‘s double portion thick cut veal chops were so succulent and juicy that he couldn’t stop talking about it all trip. As Peter Luger’s is to New York, Gene and Georgetti is to Chicago. Frank Sinatra, Will Ferrell, and even the President himself have dined here and we certainly know why.
Day 1: Friday
Friday would be our first day of exploring the city! With K+M only coming for the weekend, Saturday and Sunday were already chock full of sightseeing and tourist activities. Unfortunately (or fortunately for A), L had one last morning meeting to take care of before he was free from his conference, so A seized the alone-time-opportunity for some unobstructed shopping! L’s mid-trip lodging move to The James Hotel proved to start us in the perfect location for some Michigan Avenue cruising!
Also referred to as the Magnificent Mile, Michigan Avenue is a wide, picturesque, flower-lined thoroughfare through the heart of the Second City. With a resemblance to NYC’s Park Avenue, strolling ‘the mile’ is a destination in and of itself and a perfect location for a photo op. Overflowing with people, everyone is out enjoying the strip, and the main attraction is the shops. Progressing in price as you head further north, start with your favorite go-to staples like H&M and Top Shop, and finish up with the luxe labels you adore like Louis Vuitton and Gucci. Once you hit Chanel, take a left on to Oak Street and let the explorations continue as you gawk at absurdly huge diamonds and then pick up the latest look at Tory Burch. In search of a new ‘IT bag’ and some summer shades, the time passed so quickly as A stopped into every shop and chatted with the friendly sales force. Chicago has such amazing people!
After both shopping goals were tackled, A+L met for lunch… and to celebrate the official start of our mini-vacation together. To ring it in with Chicago style, we decided that a classic deep dish was the way to go. Heading north on Rush Street, past Mariano Park, we found the world-famous Lou Malnati’s Pizzeria and quickly found our way inside the lovely restaurant. With a history dating back to Chicago’s pizza beginnings, it was the perfect spot to taste the real thing. We devoured the super rich, sauce-topped pizza ‘pie’ and an order of their cheesy bread. A fabulous ‘first’ meal to kick off the weekend.
With bellies full of cheese and bread, we walked off some calories on the way back to the hotel… and proceeded directly to nap time. We needed to recharge. K+M had a late flight, and the four of us had a super late 11pm dinner reservation to accommodate their flight schedule. We excitedly awaited their arrival!
After a bit of a ‘bumpy’ flight, we met in the lobby and were ready for a fantastic meal… and some cocktails! Friday’s dinner was scheduled for Top Chef winner Stephanie Izard’s award winning restaurant The Girl and the Goat. Located in the hip West Loop section of town, the block was full of swank and trendy eateries… if only we had more time! The bustling ‘Goat’ was packed with patrons sucking down expertly mixed, specialty cocktails and a table full of tapas-style ‘small plates’. We fit right in! Ordering 12 items, we noshed on frogs’ legs, oysters, and various parts of the goat, with everything really impressing. The menu is quite progressive and really pushes where restaurants are heading these days! Have an open mind and be ready to step just outside of your comfort zone to experience something new and delicious.
With our late reservation, and our ability to chat indefinitely, we finally departed around 1 am… when they were literally turning the lights on. Our next stop was the Redhead Piano Bar located just around the corner from our hotel. After a short cab ride, we hopped out in front of the neon sign. We had received a recommendation for the bar from a bartender we had met in our Colorado travels… unfortunately, this tip didn’t pan out as we had hoped. Think: sing along “Piano Man,” beers and basic drinks, and really drunk patrons. We were far too sober for this type of atmosphere! After a short round of beverages, we were off to our next location, Jbar, situated right next door to our hotel. To our dismay, it was already closed! Instead, we decided to make our own cocktails back at the hotel room at the ’2+2 lounge,’ and chatted all night until the birds started chirping and the sun was beginning to rise. We New Yorkers know how to shut a city down!
After staying up until nearly sunrise, we got a few mere hours of sleep before embarking on another jam-packed day. We were in dire need of a solid breakfast that would bring us to full recovery and help us power through everything on our agenda! We had learned that the Navy Pier was a sight to see and figured there would be plenty of spots just waiting to serve up a tasty brunch. With our first food experiences reaching stellar charts, we had high hopes for all of Chicago! We certainly overestimated the quality of the Navy Pier, as we were all a bit shell-shocked upon entering. The smell of stale popcorn, crying children, and scents of sour beer wafting out of eateries was not exactly our idea of fun. We took a full stroll through the entire venue with a hope that something really good lie ahead….much to our disappointment, we only fooled ourselves. It was just more of the same! We nearly settled for a spot that seemed “okay,” but it was L who made the executive decision to hop in a cab and high-tail it out of there….regardless how starving we were, we would be thoroughly disappointed for settling and wasting perfectly good stomach space and calories. So, we were off to a place L said he hadn’t been but heard was a hit. We grabbed a cab and headed back to The Loop to S. Michigan Ave. When we arrived, A + K remembered this spot was already on the list! Hooray! Food salvation.
The Gage is an upscale gastropub just steps from Millennium Park with a fabulous brunch menu, including the essential cocktails. As soon as we were seated A and M ordered up some mimosas, while K and L went for the giant Bloody Marys. And it began….recovery! K+L knew instantly that they were going to order up the Full Irish. It has all the essentials: 2 eggs, English-style bacon, sausage, a baked tomato, white & black pudding, and a side of baked beans. Oh yea! A grappled with her decision, but knew she made the right one as she savored her Housemade Corned Beef Hash with Poached Eggs and Hollandaise. As L was a bit “over” breakfast, he selected from the lunch menu and ordered the “Regular” burger, which turned out to be anything but regular! It was outstanding….truly a feast fit for royalty!
After giving thanks for not giving our hungry bellies their way and waiting for a stellar meal, we were off to some sights! We took a lovely stroll through Millennium Park enjoying all of the blooming tulips that seemed to be singing classical music everywhere we went (we love the speakers all over town!). We made our way to the infamous Bean and took what seemed like a thousand photographs, as we were truly mesmerized by this giant sculpture. Inspired by a drop of mercury, this sculpture was selected during a contest and constructed in Millennium Park between 2004 and 2006 at Cloud Gate in the center of the park.
We continued our stroll through the park admiring flowers and architecture in every which way as we made a path to the Art Institute of Chicago. With so much on our agenda for the remainder of the day, we made an executive decision to not make a formal stop at the Art Institute. We felt with so many other unique sights in Chicago, we’d have to skip this one for now, knowing well we’d be back (and knowing how much art we’ve taken in around the world). Their regular collection boasts everything from Ancient and Byzantine art to the most contemporary works like Jackson Pollock, with specks of European Painting and Sculpture.
We were too enamored with the art outside to bring ourselves inside. So we took ourselves on a tour of Chicago’s architecture. The Great Fire of 1871 made Chicago what it is today. At the time of the devastation, it made Chicago a blank canvas, which soon attracted some of the most ambitious architects to rebuild the city. Men such as Louis Sullivan, John Root, and Daniel Burnham came to the city in hope of breaking new ground. These men were responsible for what became known as the “Chicago School.” This school used steel framing and high-speed elevators to create the modern skyscraper. While the Willis Tower (fka The Sears Tower) is among the most famous, we also couldn’t help but gawk at the John Hancock Tower and Trump Tower. Chicago’s architecture is, well, impressive! At the turn of the 20th century, Beaux-Arts and Art Deco made some appearances, furthering Chicago’s unique skyline. Buy yourself a solid guide and give yourself the architecture tour…it’s well worth it
Some other architectural pillars include ‘The El,’ Chicago’s elevated train, as well as the famous theater that boasts the Chicago musical and world-famous signage. Growing a bit tired, L suggested a stop at his previous hotel, Hilton’s Palmer House to take a short rest and to take in the beautiful lobby. We headed up to the second floor to get a bird’s eye view of the goings-on below, as well as to take a closer look at the breathtaking frescoes on the ceiling.
Feeling like we actually needed a power nap, we completed our walk along the bank of the river to make our way back to the hotel. We had fully understood how Chicago got its nickname: ‘The Windy City.’ We made our way back for a well-earned nap in preparation for our much-anticipated dinner. We may have just stopped for a few snacks at David Burke’s Primehouse, and a cocktail or two. Hey, we were on vacation!
After our cat nap, we got all dolled up (the boys, too!) and we were ready for what we didn’t know beforehand would be the star of the show: Maude’s Liquor Bar back down in the West Loop on West Randolph Street. While they call themselves a “French-infused oasis,” we felt it even had a very Speakeasy-quality to it, especially on the second level. Encompassed by exposed brick and illuminated only by candlelight, it was perhaps one of the sexiest venues we’ve ever laid eyes on! We expected nothing less than food porn from Maude’s. Boy, did she deliver!
L’s eyes were immediately feasting on the Roasted Bone Marrow as soon as we got our menus. None of us had experienced this dish before except for L, so we decided we were in it together. How can we call ourselves foodies if we turn down any food? Along with our bone marrow, we ordered an array of balanced dishes such as the Steamed Mussels with white wine, herbs, and espelette (a variety of chili pepper) and a the Roasted Asparagus with brown butter and parmesan, all of which were incredibly done! We were a bit disappointed with our overcooked gnocchi, but our server was more than accommodating when we quietly shared our thoughts. We generally don’t send things back, and we’ve learned when you really need to, it’s okay! We were so impressed with every bite, as well as our tasty libations. We were all in favorite of the Smashes, which is composed of a Spirit (Maude’s offers Vodka, Smalls Gin, Chartreuse, Smoky Violet, or Whiskey), muddled fruit, sugar, and mint. A Whiskey Smash felt the most natural, and as it turns out, this recipe “dates back to 1862 with Jerry Thomas, the god-father of cocktails and author of one of the first bar guides,” according to Maude’s blog.
After ending up on Food Cloud 9, we were fulfilled. We couldn’t imagine continuing on to another spot. We felt we had reached the ultimate. The only thing left to do was to head back to The James for an appropriate night’s sleep and give thanks to the food gods for an exceptional experience. After a long, but incredible day, we hit the pillow and hoped our weekend never had to end. Fortunately, we planned to make the best of every minute of our Sunday.
It’s the last day and we leave later this night, which means cramming all that we had yet to see and do in Chi-town in a few hours before jumping on the plane. Breakfast was a quick one: a couple of pastries from across the street, a smoothie for Ang from David Burke, and we were in a cab on our way to Wrigley Field for the walking tour of the stadium.
Whether you are a baseball fan or just a fan of American history, this is a must-do. Wrigley Field tours cost about $25.00 a person, and well worth it for very energetic and informative tour guides who take time to answer everyone’s questions. The tour takes you into the stands, through the press box, down into the visiting teams’ locker room, and into the dug out. (We had to hold Lee back from jumping over the rope and running on the field; he did get to sneak a foot on the grass and seemed happy enough.) It was great learning all the historical facts about the 2nd oldest baseball field built in America, such as how the great ivy wall was first stapled on, the curse of the Goat, the man-run scoreboard, the stands built on top of the surrounding buildings so that more people can see a home game, and about all the classic movies filmed on this field (Rookie of the Year is just one of many). Although only L is the big baseball fan, we all agreed that the tour was great and definitely a big part of America and its history. Everyone who is in Chicago should go at least once.
Then, it was onto the John Hancock building for the great observatory and views miles above the city. The weather was not the clearest; actually, it was gross out, but we thought there was some hope that we would be above some clouds up there and needed to give it a shot. We hopped on one of the fastest elevators we have every ridden in and headed to the Signature Room. Unfortunately, we were not above the clouds and the view wasn’t so great, but the cocktails looked good and we needed a snack. The cocktails were tasty, but the prices were just as high as we were, which is to be expected (you pay for the view).
Next on the list was to head over for some late lunch at the Purple Pig. Voted one of the top 10 restaurants in America, this “cheese, swine, and wine bar” is the perfect spot for us and we couldn’t wait to see what dishes they had in store. The menu is full of amazing things to choose from, but we had to narrow them down and have some self control. Marinated Olives, Milk-braised Pork Shoulder, Sardines with shaved fennel salad and lemon vinaigrette (only for L and M), and Morcilla with Pink Lady apples and watercress made the list. Everything was amazing of course and we topped it all off with the Panino con Nutella (a sweet sandwich filled with a chocolate hazelnut spread, marshmallow cream, & bananas). Don’t for get to add a scoop of ice cream.
After all that, it was still not over because we had not been to see some live jazz. How could any of us leave Chi without seeing some of the music so characteristic of this town? So we rushed back into another cab and headed to Buddy Guy’s Legends Jazz Club for the afternoon show. We had some drinks, hung out for some smooth jazz for about an hour, and then the end was here. We had to head back to pick up our bags and head back home.
This trip was a quick, yet filled with non-stop fun, life-changing food, tons of American history, and plenty of laughs! We all agreed it left us wanting more and somehow we would find some time to head back here and do it all over again and then some.
- The James Hotel Chicago (A swanky boutique hotel right off Michigan Avenue, the Magnificent Mile, with lots of hip little touches like an amazing minibar and drink menu, a stocked gym and fluffy bath robes. David Burke’s Primehouse is located inside. 55 East Ontario. www.JamesHotels.com)
- Hilton Palmer House (A stately and grand hotel and conference center with awe inspiring ceilings and a lively lobby bar. Recommended!! 17 East Monroe Street. www.PalmerHouseHiltonHotel.com)
Strolling and Shopping
- The Magnificent Mile (North Michigan Avenue, the main shopping, dining and fun drag through Chicago featuring over 400 stores and a concentration of high end hotels. Passing through Streeterville, extending up to The Gold Coast. Spend the day wandering Saks, Chanel, Louis Vuitton, Gucci, Tory Burch, and tons more. Plus plenty of everyday shopping as well like H&M, Top Shop, and Express. www.TheMagnificentMile.com)
- River North (A former industrial area reinvented into a thriving, art, dining and nightlife mecca. Check out the artist’s lofts full of contemporary displays by a younger generation. More info here.)
- Gold Coast (Upscale real estate lakeside at the north end of Michigan Avenue. Visit Division and Rush Streets for rowdy, frat boy inspired dinner and drinks. More info here.)
- The Loop (The heart of the financial district of downtown Chicago filled with soaring skyscrapers. Takes its name from the path of the Brown Line elevated train system. Lots of incredible architecture and famous Chicago landmarks. More info here.) Features the Theatre District (Productions on lovely restored stages with plenty of history.) Broadway style, low budget, and Shakespeare! www.ChicagoPlays.com)
- Shore of Lake Michigan and Navy Pier (Exploding with parks for relaxing, picnic areas, outdoor activities, dining and water sports. Check out Navy Pier for water bound activities! More info here.)
- Bucktown/ Wicker Park (A recently revitalized urban neighborhood with lots of new cantenas and off beat boutiques for fashion forward followers. More info here and here.)
- Art Institute of Chicago (Boasting a massive collection of French Impressionist paintings, among many other inspirational offerings. 111 South Michigan Avenue. www.ARTIC.com; $18)
- Field Museum of Natural History (Towering dinosaurs, prehistoric creatures and real mummies will keep your interests all day! Roosevelt Road and Lakeshore Drive. www.FieldMuseum.com; $29 All Access, $15 Basic)
- John G. Shedd Aquarium (Exotic fish and the re-creation of massive underwater habitats. 1200 South Lake Shore Drive. www.SheddAquarium.org; $35)
- Museum of Science and Industry (An interactive museum focusing on energy, computers, technology, air flight, trains and military, full of fun facts and displays. 57th Street and Lake Shore Drive. www.MSIChicago.org; $15)
- Adler Planetarium (Space! Fascinating and foreign. Learn a little bit more about the unknown. 1300 South Lake Shore Drive. www.AdlerPlanetarium.org; $12 for basic, $28 including all exhibits.)
- Frank Lloyd Wright’s Home and Museum (Witness the famous architect’s home and influences, as well as his designs in the surrounding neighborhood. 951 Chicago Avenue, Oak Park. www.GoWright.org)
- Hull House Museum (The first social settlement for immigrants started by Jane Addams. 800 Halsted Street. www.HullHouseMuseum.org)
- Willis Tower- formerly the Sears Tower (The iconic tallest building in North America with a staggering 108 floors. Visit ‘The Ledge’, [www.TheSkyDeck.com] a glass balcony protruding out of the 103rd floor, for a scary view. 233 South Wacker Drive. www.WillisTower.com)
- John Hancock Center (Another massive skyscraper with a great observation deck complete with cocktails… plus no entry free [although you end up paying for it in the cost of the drinks] and it’s open late! By far the best view is from the ladies bathroom, so fore warn everyone as you bring your camera to the toilet! 875 North Michigan Avenue. www.HancockObservatory.com)
- Navy Pier (A former military training pier converted into a busy tourist stop with carnival style games, Ferris Wheel, an IMAX theater, an ice skating rink and beer garden, among an array of casual dining and music options. Booming in the warm weather with fireworks twice a week! Waterfront. Note: To say that it’s family friendly is an understatement! If you don’t have kids, or if you don’t like kids, this place will give you hives! More info here.)
- Millennium Park (A lakeside green space hosting concerts in the gorgeous Frank Gehry Pavilion, splashing in The Crown Fountain water feature and public art exhibit, and a plethora of outdoor activities like ice skating! View the park’s most visited feature, a sculpture by Anish Kapoor, a massive, mirrored dome referred to as ‘The Bean’, or put together a waterfront picnic with friends to enjoy the view. www.ExploreChicago.org)
- Lincoln Park and the Zoo (A completely free, renovated, zoological exhibit perfect for an afternoon stroll. Plus the massive waterfront park boasts six beaches, golf, museums and a botanical garden! www.LPZoo.org; Free)
- Summer Outdoor Events (Partake in the Grant Park Music Festival and Chicago SummerDance, free festivals in Millennium Park! www.GrantParkMusicFestival.com; www.ExploreChicago.com)
- Wrigley Field (The famous stadium of the Chicago Cubs. Enen if you aren’t a baseball fan, A+K loved the historical aspects of this tour. A must-do! www.Cubs.com)
Alternate Modes of Exploration
- City Pass (Explore all of the major museum sites for one discounted price. www.CityPass.net; $59 adults, $49 kids)
- The ‘El’ Line Elevated Train System (Criss crossing the city for an inexpensive and classic way to traverse the town. www.Chicago-l.org)
Food and Drinks
- Charlie Trotter’s (Chicago’s first celebrity chef. Experience the tasting menu of this exclusive, private restaurant located in a townhouse. A recipient of numerous awards, including 10 James Beard Foundation accolades. 816 West Armitage Avenue. www.CharlieTrotter.com)
- Alinea (Grant Achatz’s renown restaurant with a massive, contemporary tasting menu. Although it costs a pretty penny, its considered one of the top restaurants in the country. 1723 North Halstead Street. www.Alinea-Restaurant.com)
- Maude’s Liquor Bar (An absolutely incredible array of perfectly mixed cocktails and indulgent and rich dishes. Dark and sexy with a throw back vibe. The roasted bone marrow is out of this world. Best meal of the trip… hands down. 840 West Randolph Street. www.MaudesLiquorBar.com)
- Girl and the Goat (Top Chef winner Stephanie Izard’s relaxed gastropub with fun goat-inspired dishes and craft beers. 809 West Randolph Street. Reservations are hard to come by. www.GirlAndTheGoat.com)
- David Burke’s Primehouse (A selection of perfectly dry-aged high end cuts of meat. 616 North Rush Street. www.DavidBurke.com)
- Sprout Restaurant (Top Chef runner-up Dale Levitski, a James Beard award winner, whips up French-American fare in an elegant, bistro style menu. 1417 West Fullerton Street. www.SproutRestaurant.com)
- Mon Ami Gabi (The Chicago counterpart to our favorite Vegas French bistro! 2300 North Lincoln Park West. www.MonAmiGabi.com)
- Bandera (Reasonable priced, but expertly prepared American dishes. 535 North Michigan Avenue. www.BanderaRestaurant.com)
- The Purple Pig (“Cheese, swine and wine”… we couldn’t say it better ourselves! A vino bar with tasty charceuterie and tapas. Voted Top 10 of New Restaurants in America by Bon Appetit magazine. Reservations are not accepted. 500 North Michigan Avenue. www.ThePurplePigChicago.com)
- Sable Kitchen & Bar (An elegant, American gastro bar serving brunch through dinner. 505 North State Street. www.SableChicago.com)
- Gibson’s Bar and Steakhouse (A classic carnivore’s dream with plenty of atmosphere and action. 1028 North Rush Street. www.GibsonsSteakhouse.com)
- The Gage (A gastropub with Irish-American fare and a stellar collection of cocktails. Fabulous brunch!! 24 South Michigan Avenue. www.TheGageChicago.com)
- Topolobambo (Traditional Mexican fare by renown chef Rick Bayless. Reservations are hard to come by… book 8 weeks in advance. 445 North Clark Street. www.RickBayless.com)
- Spiaggia (Four star fine Italian dining by chef Tony Montuano with a hefty price tag. Lovely modern, clean decor. 980 North Michigan Avenue. www.SpiaggiaRestaurant.com)
- Gene and Georgetti (A classic Chicago steakhouse and staple since 1941. 500 North Franklin Street. www.GeneAndGeorgetti.com)
- Gino’s East of Chicago (Original deep dish pizza Chicago style, with several locations around the city. 633 North Wells Street. 162 East Superior Street. www.GinosEast.com)
- The Original Pancake House (A country wide phenomenon of explosive pancake creations. 22 East Bellevue Place. www.OriginalPancakeHouse.com)
- The Violet Hour (A lavish, retro cocktail lounge in a polished atmosphere. No reservations and first come first served policy. Think pricey concoctions prepared by a mixologist. 1520 North Damen. www.TheVioletHour.com)
- The Red Head Piano Bar (An interactive cocktail lounge with a lively [but kind of weird] atmosphere and sing along. 16 West Ontario Street. www.TheRedHeadPianoBar.com)
- Buddy Guy’s Legend (An awesome little jazz club with non stop performances. Stop in for a drink and some blues. 700 South Wabash Avenue. www.BuddyGuys.com)
- Green Mill Cocktail Lounge (Check out rising jazz artists as they perform in a piece of 1930s music history with a link to the notorious Al Capone. 4802 North Broadway Street. www.GreenMillJazz.com)
- House of Blues (Concert venue, dining and drinks in this staple Chicago location! Features the lively Sunday morning Gospel brunch. 329 North Dearborn Street. www.HouseOfBlues.com)
- Comedy Shows (Chicago is a mecca of rising comedy stars like our favorite, Tina Fey!