NIGHTLIFE – DINING – SHOPPING – HOTELS – TOURIST ATTRACTIONS
A Chicago travel guide has been highly requested and is long overdue. I’ve been putting this one off due to the fact that every time I’m in Chicago, I add new favorites to my list. Chicago is one of my absolute favorite cities, which made it kinda hard for me to move to Florida this past year. I love having four seasons and how cool the city looks whether it’s sunny or snowing.
“What are the best things to do and places to eat in Chicago?” is a question I get all the time. If you live in the Midwest, Chicago is a perfect weekend getaway that you can probably drive to. Between the Magnificent Mile shopping, museums, Chicago Riverwalk, boat tours, sporting events, and some of the best food, there’s SO much to do and see. I’m sharing some of the top-rated things to do, places to eat, hotels to stay at, and what to see when you’re in the Windy City. This will be a continuous work in progress and I will keep adding to this post as my list grows!
If you are just in town for the weekend, I always suggest that people stay off of North Michigan Ave, in River North, or in The Loop (just south of the river). These are three of the most convenient locations and are just a short walk from each other. Up and down North Michigan Avenue is where all of the major shopping is. You can find tons of luxury hotels here, but they can be pricey. If you stay in River North – where lots of bars, restaurants, and nightlife are – you can walk to Michigan Ave in a few minutes. The Loop, where I used to live, is also really convenient and super close to Millennium Park (the famous Bean sculpture) and just a few blocks from the Riverwalk and Michigan Ave. I will link some of my favorite and most convenient hotels below, too. Enjoy 🙂 Xx
Food & Drink
Gibson’s Italia – $$$$ – River West – Amazing food, drinks, and a stunning view of the river from their new patio and 4th floor rooftop.
BLVD – $$$$ – West Loop
Mastro’s – $$$$ – River North
Tao – $$$ – River North
RPM Steak – $$$$ – River North – Must try the 24k gold chocolate cake.
RPM Italian – $$$ – River North – Amazing desserts.
Rosebud Italian on Rush – $$ – Gold Coast
Noyane Rooftop – $$$ – Michigan Ave
Osteria Via Stato – $$ – River North
Bavette’s Bar & Boeuf – $$$$ – River North
Beatrix – $$ – Multiple Locations – Great for a quick breakfast or brunch.
Steak48 – $$$$ – River North
RPM on the Water (Coming Soon) – $$$$ – On the River
Prime & Provisions – $$$$ – The Loop
Bar Siena // Bombo Bar – $$ – West Loop – All-time favorite brunch, lunch, or dinner spot! Don’t leave without getting their Bombo donuts.
Shake Shack – $ – Michigan Ave S (in Chicago Athletic Association) – My absolute favorite for burgers & cheese fries.
Portillo’s Hotdogs – $ – Multiple Locations – A must when in Chicago.
HoneyGrow – $ – Multiple Locations – My favorite for a super quick lunch.
Summer House Santa Monica – $$$ – Lincoln Park
3 Arts Club Cafe (at Restoration Hardware) – $$$ – Gold Coast – Definitely Insta-worthy.
Maple & Ash – $$$$ – Gold Coast
Carmine’s – $$ – Gold Coast
Luxbar – $$ – Gold Coast
Hampton Social – $$ – River North
Siena Tavern – $$ – River North
Tavern on Rush – $$ – Gold Coast – Fun outdoor patio seating for brunch.
Public House – $$ – River North – Must try their cake shakes!
Moe’s Cantina – $$ – River North
Broken English – $$ – Multiple Locations
Remington’s – $$$ – The Loop
Bar Lupo – $$ – River North
Eataly Pizza & Pasta – $$ – River North
Parlor Pizza Bar – $$ – West Loop
The Dawson – $$ – River West
Piccolo Sogno – $$$ – River West
Mercadito – $$ – River North
Grand Luxe Cafe – $$ – Michigan Ave
Lou Malnati’s Deep Dish Pizza – $$ – Multiple Locations
Giordano’s Deep Dish Pizza – $$ – Multiple locations
Sweets // Coffee
Stan’s Donuts & Coffee
Goddess & The Baker
Sprinkle’s Cupcakes & Cupcake ATM
Joe & The Juice
Cocktail Bars & Nightlife
Fremont – River North
Bounce Sporting Club Chicago – River North
Joy District // Rooftop – River North
Bub City // Live Country Music – River North
Celeste – River North
Federale’s – West Loop
Prysm Nightclub – Lincoln Park
Concrete Cowboy – River North
Paradise Park – Wicker Park
Waydown Rooftop (Ace Hotel) – West Loop
LIQRBOX – River North
Headquarters Beercade // Arcade Bar – River North
IO Rooftop (Godfrey Hotel) – River North
Bottled Blonde – River North
Cindy’s Rooftop – The Loop
London House Rooftop – The Loop
Trump Terrace Rooftop – On the River
Raised Rooftop (Renaissance Hotel) – The Loop
Up & Up Rooftop at The Robey Hotel – Wicker Park
The Renaissance on Wacker – $$$ – Loop
Residence Inn & SpringHill Suites (connected) – $$ – River North
theWit Hotel – $$$ – Loop
London House on Wacker – $$ – Loop
Virgin Hotel – $$ – Loop
The Gwen (Connected to Nordstrom) – $$$$ – Michigan Ave
Conrad – $$$$ – Michigan Ave
Hotel Chicago Downtown – $$$ – Michigan Ave
The Langham – $$$$ – Michigan Ave
The James – $$$ – Michigan Ave
Omni Chicago – $$$$ – Michigan Ave
The Westin Chicago – $$ – Michigan Ave
The Westin Chicago – $ – River North
The Ritz Carlton – $$$$ – Michigan Ave
The Godfrey Hotel – $$$ – River North
MOXY Hotel (New) – $$$ – River North
Aloft Chicago – $$$ – River North
Kinzie Hotel – $$$ – River North
Ace Hotel – $$$ – West Loop
Anywhere off of North Michigan Avenue!
N Michigan Ave – Nordstrom, Saks Fifth Avenue, Neiman Marcus, Macy’s, Forever21, Sephora, Ulta, Zara, Water Tower Place, high end designer boutiques, etc.
State St (Loop) – Macy’s, Zara, Magnolia Bakery, Urban Outfitters, Forever21, Sephora, mostly popular chain retailers
Touristy Things To Do
Riverwalk – Have drinks, dinner, or coffee along the Chicago river. You can access the riverwalk at different points along Wacker Dr and you’ll find places like City Winery, Tiny Tapp, and Chicago Cut Steakhouse overlooking the river.
Boat Tours – If the weather is good, you have to take a boat tour through and around the River. I highly recommend the Wendella Architectural Boat Tour – they even serve drinks on the boat.
Chicago Water Taxi
Millennium Park – Take a picture with the famous mirrored bean sculpture, or see the sculpture from Cindy’s Rooftop Bar across the street.
Cub’s Game in Wrigleyville – This is definitely one of the top rated things to do in Chicago. Wrigleyville is also packed with bars and restaurants to check out before or after the game.
Chicago Bull’s Game at United Center
Navy Pier – Grab food and check out the Ferris Wheel.
360 Chicago – Observation deck located on the 94th floor of the John Hancock building. You can also view the city from their tilting glass observation deck.
The Signature Room at the 95th Floor – Have brunch, lunch, dinner and/or drinks on the 95th floor of the John Hancock building with an amazing view of Chicago.
Museums – Chicago’s famous ‘Museum Campus’ is where you’ll find the Shedd Aquarium (highly recommend), Adler Planetarium, Field Museum, and Soldier Field, where the Chicago Bears play. Museum Campus also has an amazing view of the city skyline.
Oak St Beach
North Avenue Beach
Eat & Drink – I can honestly say that Chicago has some of the BEST food, restaurants, lounges, and rooftop bars. These alone are some of my favorite things to do in this city 🙂