Chicago

Where To Eat & Drink

Chicago Staples: Deep Dish Pizza, Hot Dogs, Italian Beef etc.

Portillo's ♡♡* : the best Chicago style hot dogs & italian beef (order dipped with hot peppers & cheese!) Just do it.

Lou Malnatis or Giordanos : most popular Chicago deep dish spots - several throughout the city, we like Lou Malnatis!

Pequods ♡ : the best Chicago pizza in the city, however, a bit of a hike (worth it though)! – Lou Malnatis & Giardanos are easier to  access downtown

Al's Beef : also famous for Italian Beef (arguably a better Italian Beef than Portillos. I disagree, depends who you ask) & Hotdogs

Parlor Pizza , Siena Tavern (or Bar Siena), Piece Pizza : Regular pizza (not Chicago style)

Brunch

3 Arts Cafe (at Restoration Hardware)♡♡ : This restaurant is part of Restoration Hardware in the Gold Coast. It is one of the most amazing concepts, gorgeous cafe/atrium downstairs, great for brunch, lunch or dinner. Be prepared to wait 1-2 hours however, you can walk around the 5 floors of gorgeously decorated rooms & have a drink while you walk around. They also have snacks (croissants & cookies) to tide you over while you wait. Bonus, you can get the Au Cheval burger here (best burger in the city - listed below) if you’re craving a burger!

Beatrix : Healthy & delicious breakfast options! I recommend getting a reservation. Great decor, service & food.

Hub 51 : a ton of options - something for everyone type of place, typically can get in easily without a wait & have a great mimosa deal

Hampton Social : Hampton style bar/restaurant (good for dinner or cocktails too!) 

Summer House Santa Monica ♡ : Beautifully decorated restaurant that makes you feel like youre in Santa Monica, California. Awesome food and decor. Its a little bit of a hike from downtown but Lincoln Park is beautiful and worth walking around!

Casual & Affordable Food

Quartino Ristorante ♡ : Fun family/tapas style Italian restaurant. This is my go-to with groups because its fun, cheap, great food, fun atmosphere! One of my favorite and most frequented restaurants in Chicago. Their Neapolean style pizzas, penne al la vodka & tortellini alfredo are my favorites!

Eataly : Italian market, great for walking around & shopping. There are also great restaurants inside of the market where you can sit and enjoy a casual or fancy meal. 

Ramen San : Fun 90s rap Ramen spot in the heart of River North and another location in West Loop. Excellent food, great prices, fun atmosphere. They also have a similar themed sushi restaurant nearby called Sushi San - highly recommend as well!

Parlor Pizza  : Bar style pizza place. Great pizza, patio and great for watching games.

Green Street Smoked Meats : Texas Style BBQ - fun atmosphere with a bar in the center of the restaurant. Very casual

Au Cheval /Small Cheval ♡ : best burger in the city- can be a good 2 hour wait depending on what time you go at.  They will text you when you’re table is ready. Au Cheval is a nicer sit down with other menu options. Small Cheval is more of a take out/casual spot for a quick burger - no wait really (only serve shakes, burgers & fries). You can also get their burger at Three Arts Cafe at Restoration Hardware.

Tank Noodle : If you want the best Pho intown and find yourself in Andersonville, definitely hit Tank Noodle. Its amazing, cheap & BYOB. I love their brisket pho and their #12 Tank’s Crepe is a MUST ORDER. Its a shrimp, pork belly crepe - hard to describe but just do it!

Foodie & Mid-Range Dinners

Rose Mary ♡♡ : Rose Mary is definitely the best new restaurant in Chicago this summer. Michelin Star Chef (Spiaggia) & Top Chef winner , Joe Flamm, started his own Croatian/Italian restaurant in the West Loop and its incredible. Start to finish, the food, drinks, service and ambience are incredible. Rose Mary has a great wine list and also several different spritzes, all worth trying! We tried about 11 of the dished on the menu and all were absolutely delicious. The stand-out menu items were the spinach cappelletti (with shaved truffles!), lamb ragu, octopus and the pork ribs. The ribs are actually to die for and a must order (careful, they’re spicy if you don’t like spice!). The dishes were perfectly paced out and made for a perfect evening out! I recommend going with 4 people so you can try more menu items.

Girl & The Goat ♡♡: famous Top Chef - Stephanie Izard - very different/fun for adventurous eaters! Make reservations a few months/weeks out - arguably the best restaurant in Chicago.

Topo Gigio ♡: Excellent Italian food, big portions, nice patio (old school Italian) – my favorite Italian restaurant

Tanta ♡ : Excellent Peruvian food (one of my favorite spots in Chicago), awesome rooftop in the summer.

Aba ♡ : Israeli food – delicious & fresh tasting – great wine list – great for a lighter dinner- cool patio in summer

HaiSous: Favorite spot for amazing Vietnamese food in Pilsen. Get the Bun Cha!

Giant ♡: High quality food if you venture up to Logan Square. Very creative & delicious dishes, unpretentious. Excellent cocktails as well!

Beatnik / Beatnik on The River : One of the most gorgeous restaurants in Chicago. Ambiance for days with their Boho style decor. Mediterranean fusion food & excellent cocktails. Drop in for a drink or dinner.

Fancy Restaurants & Steakhouses

Bavettes ♡♡ : By far my favorite steakhouse in the city. Speak easy style restaurant (different than your typical steakhouse ambiance). Excellent cocktails, sides & seafood as well. Their NY Strip, Mashed Potatoes, Seafood Tower are must haves in my opinion.

Maple & Ash ♡: Swanky swanky steakhouse, very cool vibe, excellent steak.

GT Prime : Modern style steak house. Tapas style, great sides, apps and small plates. Great if you’re looking for a treat and something different.

RPM Seafood : Fancy seafood & steak house on the River. Incredible views of the River Walk with excellent food. Modern/trendy

Next : Part of Alinea group & has a Michelin Star. Tasting menu typically as a theme by country (buy tickets ahead for your meal, wine pairing, and even tip) - pricey but fun culinary experience.

Alinea ♡ : If you want to try a 3 Michelin Star meal, go here. It’s been named the #1 restaurant in the world multiple times. Chef Grant Achatz is a culinary genius that is extremely creative and takes risks. This is a “once in a life time “ meal and will run you about $500/person. Tickets open about 2.5 months before you can get a reservation and buy your experience in advance (wine, meal, tip, tax). This is not refundable but needs to be planned in advance. They sell out quick. I was only able to do try Alinea:Air which they put together during COVID on a rooftop. Food & wine were incredible and creative - I was impressed with what they were able to do in such short time. I didn’t get the “full experience” of their original location but loved it nonetheless. My husband and I split the wine pairing and it was very generous! I would have left pretty drunk had I ordered my own :)

Chicago Cut , Gibsons or Gene & Georgetti : Classic/Old School Chicago Steak Houses. Not my personal favorites but a lot of people love these spots!

Drinks & Going Out

Chicago Athletic Association : One of the most gorgeous hotels in Chicago. Their rooftop bar (Cindy's) overlooks Millennium Park and Lake Michigan. You can grab a drink & appetizers and see a gorgeous view of the city. Downstairs there is a game room with billiard tables & bocce ball etc

Untitled Supper Club ♡ : Speakeasy, very fun dance floor. Normally live music/burlesque shows prior to it becoming a dance floor (they also do a nice dinner here!)

Drum Bar : Great rooftop. Great for whiskey & scotch lovers. 

Theory ♡ : Awesome sports bar in the middle of River North. It is a Patriots bar so I frequent it often! The owner Joel goes above & beyond for customer service and will treat you like gold. They will have all of your favorite bar foods but do it better than anywhere else (they even have great healthy options like hummus platters, wraps, salads, bowls). Their buffalo strips, tater tots, buffalo mac & cheese and cookie skillet are worth a stop in.

Joy District : Gorgeous rooftop, three story bar. After 9-10PM it gets a bit clubby

Three Dots & a Dash : Tiki Bar restaurant, very cool, excellent/fun cocktails! This is my go-to with out of towners - especially in the dead of winter.

Cabra / The Hoxton ♡ : The Hoxton Hotel has an awesome lobby bar & also a rooftop restaurant with excellent cocktails (Cabra - great food here as well if you can get a table)

Where To Stay

If I were staying in Chicago for the first time, I would stay in either the River North, Gold Coast or West Loop neighborhoods

River North

• Westin River North / Downtown : Right on the Chicago River Walk - amazing views in all directions. Easy to get anywhere downtown from here or West Loop

• The Kinzie Hotel : In the heart of downtown / River North

• Aloft (River North) : In the heart of downtown / River North. Great brunch at their restaurant on the first floor (Beatrix). The Aloft typically has pretty reasonable rates

Gold Coast/Old Town

• The Lincoln : Great hotel in the heart of Old Town. Awesome rooftop bar over looking Lake Michigan. Easy access to the lakefront trail / beaches. Close to Second City, Wells Street (great bars & restaurants) and not far from downtown

• Viceroy Hotel : In the heart of Gold Coast - amazing shopping & restaurants near by - easy access to downtown/River North/West Loop. There is a great restaurant on the first floor, Somerset.

West Loop

• The Hoxton : In the heart of West Loop - excellent hotel lobby bar & rooftop restaurant (Cabra). Walking distance to Chicago’s best restaurants (off Randolph Street)

• Ace Hotel : In the heart of West Loop - I have never been but hear there is an excellent restaurant for brunch or dinner (City Mouse) & rooftop bar. Walking distance to Chicago’s best restaurants (off Randolph Street)

Things To Do

Architecture Tours : One of the best attractions is the river & lake architecture tour. There are several companies that offer the tour – we highly recommend taking one that is both river and lake. Wendella Boats & Shoreline Sightseeing are two popular companies to go through.

Chicago Riverwalk ♡♡ : Walk along the Riverwalk between River North & The Loop. It is a beautiful walking path with many options for food & drinks - City Winery is great, there are a ton of other patio options too.

Charter A Boat ♡: Lake Michigan is beautiful - a day out on the Lake/down the river downtown with the skyline in the background is an amazing & memorable experience. For partiers, ask your captain to head to the Play Plen

Comedy Show ♡♡: If you’re looking to catch an awesome show, head to The Second City and check out their Main Stage or ETC Stage shows. I would booked about 3 weeks in advance, they sell out for the 8:00 time slot. This is sketch comedy and a lot of SNL actors/actresses come from here (Chris Farley, Steve Carell, Tina Fey, Amy Pohler etc). For awesome stand-up, head over to Zanies .

Sports Games - Chicago is a huge sports city, worth checking out one of the local sports teams!

• Cubs (Baseball)♡♡: games are fun for the atmosphere and all of the shops, bars and restaurants around the stadium. Tickets are quite pricey but a very fun option.  Check out the rooftops too for an all-inclusive deal (food, drinks, indoor seating and stadium seating outside the stadium that looks INTO the stadium- it is not INSIDE Wrigley Field but can see the game) - easy access via the Red Line CTA

• White Sox (Baseball): games are much more affordable and more about the baseball than the “baseball atmosphere / drinking”.  ½ the stands are empty for most games – no bars/restaurants around the stadium – food inside the stadium is actually quite good with a lot of options! - easy access via the Red Line CTA

• Bears (Football): I am a huge football fan & Bears games at Solider Field are a blast if you can get an affordable ticket! A little bit of a walk from the Red Line but definitely walk-able!

• Blackhawks Games (Hockey)♡: The energy at the United Center is amazing - Blackhawks games are some of my favorite Chicago sports games to go to. Chicago is a BIG hockey town! United Center isn’t super easy to get to via train but there are buses from the Loop that will get you there (or go early & Uber)

• Bulls (Basketball) : The energy at the United Center is amazing - I am not a big NBA fan so might not be the best to ask here. Typically you can get tickets easily/cheap

Shopping : If you stay in the River North or Gold Coast neighborhoods, head to Chicago's "Magnificent Mile" for all of its shops. Many of these stores are the same ones you have at home – and as a warning, Chicago sales tax is a whopping 10.25%! Regardless- its fun to walk around & shop.

Go to Restoration Hardware & 3 Arts Cafe ♡♡ (also in the brunch section) This is part of Restoration Hardware in the Gold Coast. It is one of the most amazing concepts, gorgeous cafe/atrium downstairs, great for brunch or lunch. Be prepared to wait 1-2 hours however, you can walk around the 5 floors of gorgeously decorated rooms & have a drink while you walk around. They also have snacks (croissants & cookies) to tide you over while you wait

Hancock Tower : Incredible views of the lake & city. It is walking distance from both hotels. There is an observatory at the top of the building which you can pay to get in to : 360 Chicago. However, we recommend avoiding the crowds of tourists, and instead of paying an entrance fee – enjoy the exact same view while you enjoy a cocktail at the Signature Lounge on the 96th floor.

Willis Tower Sky Deck : Yes Chicagoans still call it the Sears and it's still the "Tallest Building in The World" ;) If you're brave, walk out on "the ledge".

Millenium Park : This park is host to many events throughout the summer - and home to the giant bean. It is a beautiful park and worth a visit. It is also right next to the Art Institute and easy to knock both out together in one afternoon.

Museums : There are numerous great museums throughout Chicago. Some of our favorites include the Art Institute of Chicago and the Shedd Aquarium. Other attractions on museum campus include the Field Museum (home to Sue the T-Rex), the Adler Planetarium and Soldier Field.

Navy Pier : This the most popular tourist destination during Chicago summer. It is a nice walk along the lake & beautiful view if you go to the end of the pier. There are tons of shops, restaurants & things to do (including rides & a Ferris Wheel). There is also a Children’s Museum there. As a warning, this will be packed with kids, families & tourists.

Lincoln Park Zoo : The Lincoln Park Zoo is one of the oldest in the country, open 365 days a year and one of the best destinations for visitors and locals alike because it is completely free! Its a bit of a trek from both downtown

* Winter Happenings *

Christkindl Market ♡ : There is a German Christmas festival in both the Loop off of Michigan Ave and another right next to Wrigley Field called Christkindle Mart – its really fun, you can get malt wine & shop for holiday gifts/décor. If you have a big group, you can reserve tables ahead for a minimum for food & drinks. It’s definitely a great way to beat the crowds and have a more enjoyable experience!

Michigan Avenue : Chicago does a beautiful lighting right around Thanksgiving until New Years. Michigan Avenue is beautifully decorated with a big tree along with the store fronts. It’s worth walking around with some Hot Cocoa from Ghiradellis to see

Lincoln Park Zoo Lights : Lincoln Park Zoo does an annual lighting with 2.5 million lights around the zoo. They sell hot cocoa (regular & spiked!) for walking around. Great for families and couples

* ♡ = a favorite

♡♡ = a must do