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 ūüôā 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 Р$$ РGold 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 Р$$ РRiver 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

Magnolia Bakery

Do-Rite Donuts

Firecakes Donuts

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 РWicker 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 РObservation 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 РHave 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

Merchandise Mart

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 ūüôā






Chicago, Tips, Travel Guides
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