The Complete Traveler's Guide to Chicago What to Do in the City

A Weekend in Chicago Itinerary

Chicago is one of my favorite cities in the United States. They have nearly 100 museums, 23 Michelin Star restaurants (read What Are Michelin Star Restaurants?) if you’re not sure what these are), a dozen 5-star hotels, tons of fantastic events, festivals, musical performances, and pop-ups around the city, world-class luxury shopping, and so much more. We’ve visited more than a dozen times in the last couple of years, and we always find something new to love in the Windy City, which is why I wanted to share my favorite things to do in this Chicago itinerary. I hope this Weekend in Chicago Itinerary helps you plan the perfect luxurious weekend getaway to Chicago, whether it’s for a mini-honeymoon, family vacation, an anniversary trip, or to simply explore somewhere new!

Viceroy Chicago 5-Star Luxury Hotel in Historic Gold Coast District Illinois Midwest Luxury Hotels by Annie Fairfax Where to Stay in Chicago Streamline Luggage

Day 1

Arrive at Chicago
via Chicago O’Hare (ORD) Airport or connecting highways (1-55, I-90, I-94, I-290,&  I-294)

Check into Hotel
Most recently, we stayed at the 5-Star Viceroy Hotel which has a gorgeous Art Deco interior.

Steamline Luggage at Viceroy Chicago Hotel with Burberry Leather Tote Bag by Annie Fairfax

Lunch at Shanghai Terrace
Consistently voted the best Chinese food in all of Illinois, Shanghai Terrace has a fantastic, authentic menu featuring Shanghainese and Cantonese dishes with a view above the Magnificent Mile. If the weather permits it, ask for a table outside and enjoy the incredible views of the city.

Golden Shrimp Shanghai Terrace Cantonese Delicacies Best Chinese Food in Chicago Award Winning Rooftop Dining Luxury Restaurants Midwest

Explore Chicago Using CityPASS
CityPass tickets allowed us to explore Chicago’s most popular attractions like Shedd Aquarium, Skydeck Chicago, Field Museum, Art Institute of Chicago, and the 360 Chicago Observation Deck.

The Art Institute of Chicago in Chicago, Illinois by Annie Fairfax

There are two other options in the Chicago ticket as well, including the Museum of Science and Industry and the Adler Planetarium, both of which are quintessential Chicago attractions. CityPASS tickets saved us 49% off the regular price, and allowed us to skip the ticket lines in Chicago.

The Complete Traveler's Guide to Chicago Adler Planetarium

While it’s not included in the CityPASS tickets, a ride on the Navy Pier Ferris Wheel is also an iconic thing to do in the city.

Dinner at Alinea, Chicago’s Best Restaurant
Alinea is Chicago’s only 3 Michelin Star restaurant, and one of the country’s top rated dining experiences. The staff here are tremendously helpful and attentive, the food is unbelievably delicious, and the plating and molecular gastronomy techniques are something you simply have to see to believe. If you’re in the market for a one of a kind meal in the city, Alinea is the place to visit.

A meal at Alinea is really the highlight of my weekend in Chicago Itinerary, and I hope you get the chance to enjoy this incredible restaurant someday soon!

Return to Hotel

Navy Pier Ferris wheel What to do in Chicago

Day 2

Brunch at Summer House Santa Monica
This California themed restaurant has plenty of gluten-free and vegan options all in a sun soaked, West Coast inspired space.

Tuna and Watermelon Tartare Summer House Santa Monica Vegan Friendly Gluten Free Restaurant in Chicago, Illinois Gold Coast by Annie Fairfax

Relax & Unwind at AIRE Ancient Baths

Inspired by the original AIRE Ancient Baths in Sevilla, Spain, where peace, tranquility, and relaxation are held in high regard, AIRE Ancient Baths brings a slice of this incredible experience to the hustle and bustle of Chicago, creating a unique, restful space in the heart of one of America’s largest cities. Be completely transported to an intimate, quiet, candlelit space where time does not exist, and soak your cares away as you breeze from bath to bath, each with a different temperature, restorative property, and atmosphere.

AIRE Ancient Baths Spa and Wellness Haven in Chicago, Illinois Luxury Spas of the World Waiting Room

View my video tour of AIRE Ancient Baths, here.

AIRE Ancient Baths Spa and Wellness Haven in Chicago, Illinois

Explore More of the city with CityPASS
Take in more of the sites of Chicago that you might have missed on Day 1

The Official Traveler's Guide to Chicago by Annie Fairfax Where to Eat, What to See and What to Do in the Windy City

Visit a Botanical Garden
Enjoy a slice of nature in the Windy City by visiting one of the city’s most beautiful parks.

Navy Pier Conservatory What to do in Chicago

Chicago Botanic Garden The city’s largest botanic garden, this garden houses gardens from Japanese styles, English gardens, and more, as well as one of the nation’s largest collections of rare botanical literature.
Garden of the Phoenix An Authentic Japanese garden that celebrates the friendship between sister cities Osaka and Chicago.
Lurie Garden Beautiful during any season, this garden, trimmed with 15 foot high hedges, evokes classical art and French and English garden themes.

View from Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady

Take an Architectural Tour by Boat
Take the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady, and learn about the history of Chicago, its unique buildings, and the history of architecture and its influences on the rest of the Midwest. It’s also a great way to see the city from a new perspective, because everything looks completely different from the water, and many buildings were originally designed facing the river.

The Official Traveler's Guide to Chicago by Annie Fairfax Where to Eat, What to See and What to Do in the Windy City

Dinner at Pizzeria Portofino
This cute coastal Italian inspired spot serves everything from fresh pizzas and pastas to Italian cocktails and more all inside of a lovely coastal themed restaurant. If the weather is nice, ask to sit out on the patio.

Pizzeria Portofino Italian Restaurant in Chicago by Annie Fairfax Spinach and Artichoke Dip

Return to Hotel

Day 3

Brunch at Somerset Inside Viceroy Hotel
This Art Deco restaurant has some of the best brunch foods and drinks in the Midwest. You’ll love the charming atmosphere, prompt service, and fascinating dishes that lead your mouth on a world tour featuring flavors from Europe, Asia, North America, and beyond.

Check Out of Hotel
Grab your bags and get ready for some incredible shopping! Trust me, you’ll want to pack your new finds up for the trip home (if you can resist wearing them immediately), but don’t worry, our next stop will hold your bags for you while you browse.

Viceroy Chicago 5-Star Luxury Hotel in Historic Gold Coast District Illinois Midwest Luxury Hotels by Annie Fairfax Where to Stay in Chicago

Head to Fashion Outlets of Chicago
Every store here is an outlet offering discounted or on sale, completely authentic designer clothing, shoes, accessories, home furnishings, and so much more. Featuring stores like Burberry, Tory Burch, Moncler, Prada, Gucci, Pandora jewelry, Jimmy Choo, Theory, Vineyard Vines, and many more all at steep discounts (no direct to outlet pieces here either!) this is hands down my favorite place to shop in the Midwest. During my last trip, I scored nearly a dozen Pandora charms and a new bracelet at about 70% off, a leather Burberry tote bag for 70% off a Tory Burch Fleming bag at 40% off, and a few other things I’ll share soon.

Ask their concierge to hold your bags and luggage for you while you shop, so you don’t have to backtrack to your hotel. This is especially great if you’re visiting during a layover from the nearby Chicago O’Hare airport!

Depart Chicago

I hope you loved this Weekend in Chicago Itinerary, filled with my favorite things to eat, see, and do in the Windy City. Would you like to see a longer itinerary with more ideas of things to do in Chicago? Let me know in the comments below, and let me know what you’d add to this Weekend in Chicago Itinerary!

The Art Institute of Chicago in Chicago, Illinois by Annie Fairfax

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3 Comments

  1. Love Chicago! Thanks for the recommendations!

  2. My number one tip for travelers after living in Chicago, and growing up just outside of Chicago, do not visit late November-late March/April. Chicago is a city that deserves to be walked through. It’s amazing!!

  3. Saving this for my upcoming Chicago trip

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