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Chicago 3 Day Itinerary: For Luxury Travelers

Note: This post is sponsored by Enjoy Illinois. However, as always, all opinions are my own. 

Looking for the best Chicago itinerary? This itinerary for three days in Chicago is perfect for the discerning luxury traveler. 

Chicago is a bustling city with some of the most beautiful architecture in the world. While the Windy City is known for sights and casual foods (deep dish pizza!), it also has incredible high-end hotels, fine dining, theater and luxury shopping, making it the perfect destination for a long weekend trip.

I recently took this amazing fall trip to Illinois. If this post inspires you to travel to Illinois, make sure to check ahead for up-to-date events, exhibits and opening hours at any attractions.

Keep reading for the best 3-day Chicago itinerary for luxury travelers!

If you’re looking for more ideas and information about traveling to the beautiful state of Illinois, check out Enjoy Illinois. Their website is full of itineraries, destination information and more!

Smiling brunette woman standing in front of the Chicago River with a row of skyscrapers in the background.

When to Visit Chicago

Chicago is a vibrant city year-round. However, in terms of weather, the best time of year to visit Chicago is between April and early November.

Spring

In the spring months, Chicago is beautiful as the weather warms up. There might be some rain during your visit, but April showers bring May flowers!

Summer

In the summer, Chicago turns into a beachside city. The Lake Michigan waterfront is lined with beaches and there are summer boat cruises you won’t want to miss. Plus, many of the city’s restaurants have outdoor patio seating.

Fall

In the fall, Chicago has beautiful fall foliage in its many parks, and moderate temperatures. When I visited in early November, the weather was in the 70s!

Winter

If you don’t mind the cold, Chicago is a festive city to visit in December for the holiday season. For those planning a Chicago trip outside of Christmas in the winter months, the temperatures might be chilly, but you’ll be able to explore with fewer crowds.

A brunette woman in a black dress is facing away from the camera with the Chicago skyline at night in the background.

Getting to Chicago

Chicago is accessible from pretty much anywhere in America. Illinois is in the middle of the country, so it’s easy to get to Chicago by airplane, car, bus and train.

By Air

Chicago O’Hare International Airport (O’Hare) is a huge national hub and one of the largest airports in the USA. I took a direct flight from New York City to O’Hare, and my travels to Chicago couldn’t have gone smoother. 

You can also fly into Chicago Midway International Airport, which is Illinois’s second busiest airport. 

From either airport, you can take a taxi, Uber or Lyft to your accommodations. Or, you can take a Chicago Transit Authority “L Train” to downtown Chicago. You can also take a GO Airport Express shuttle to your hotel.

By Car

Chicago is an easy road trip if you’re coming from other parts of the Midwest. Chicago is accessible via these interstates and highways: 

  • I-90 (Kennedy Expressway),
  • I-94 (Dan Ryan Expressway),
  • I-55 (Stevenson Expressway),
  • I-290 (Eisenhower Expressway), and
  • I-294 (Tri-State Tollway).

By Bus

Multiple bus companies have routes to Chicago, including Greyhound and MegaBus.  

By Train

Do you prefer to ride the rails? You can travel to Chicago by Amtrak train and from the Chicago suburbs via the Metra Rail.

Getting Around Chicago

It’s so easy to get around Chicago. You don’t need to rent a car to explore the city. These are the best options for getting around the city during your 3-day trip to Chicago.

Walking

Our Chicago 3-day itinerary focuses on the extremely walkable city center. Other than getting to and from the airport, if you follow this itinerary, you can explore the city on foot.

Public Transit

Chicago has great public transportation and the Chicago Transit Authority’s “L Train” system is easy to navigate.

Taxi/Uber/Lyft

If your feet are sore or you’re running late, you can always hop into a taxi, Uber or Lyft, which can zip you around downtown Chicago.

Where to Stay in Chicago 

The Langham Chicago 

I stayed at The Langham, Chicago and can’t recommend it enough. This luxury hotel in Chicago has a convenient location, beautiful rooms, stylish common areas, and excellent amenities. 

Our room had city views, a walk-in rain shower, a big soaker tub and a separate sit-down vanity area. 

The Langham, Chicago also has an acclaimed spa, indoor swimming pool, hydrotherapy hot tub, steam rooms and saunas. It’s a perfect choice for a luxurious stay in Chicago.

A marble bathroom hotel bathroom with dual sinks, a glassed in shower and deep bathtub.
A luxury hotel room with two beds that have white sheets and brown bedskirts.
The interior of a luxury hotel lobby at night with cream couches and chairs, dark wood accents, and metallic round light fixtures hanging from the ceiling.
A luxury hotel lobby in Chicago with cream armchairs, large lamps and a marble statue of a person's head.

Other Luxury Hotels in Chicago

Chicago is home to many other luxury hotels for your trip to Chicago. Some other excellent options are:

Map of Your 3 Days in Chicago

Need help navigating the city during your stay? This handy color-coded map includes all of the places in our itinerary.

The blue pins are your day one stops, the red pins are for day two, and the green pins are the day three locations.

Day 1 (Chicago 3 Day Itinerary)

Let’s jump into your first day in Chicago. Day one is all about eating well at iconic Chicago restaurants, exploring Chicago’s downtown core, and checking out the top luxury shops in the city.

Morning 

Arrive in beautiful Chicago and make your way to The Langham, Chicago hotel (330 N Wabash Ave., Chicago, IL 60611).

Head to the second floor to see if your room is ready. If it is, then check in. If your room isn’t ready yet, check your bags with the concierge on the ground floor.

Now, head out to explore and get your bearings!

Lunch

Walk about 15 minutes to the art-filled RL Restaurant (15 E Chicago Ave., Chicago, IL 60611).

RL Restaurant is an upscale Ralph Lauren restaurant that serves American cuisine. The bar and dining room have a classic, refined atmosphere. 

The menu includes dishes like shrimp cocktail, chopped salads, Dover sole and more. I went with a glass of prosecco to kick off my trip, and then an avocado and crab salad. 

Two women's hands holding champagne glasses at a restaurant and clinking them together.
Brunette woman sitting in an elegant restaurant in Chicago. She smiling and holding a glass of champagne.
Two tan leather boothes in an upscale restaurant with white table clothes, and high end place settings.

Afternoon

After lunch, check out the Ralph Lauren store next to RL Restaurant. The staircase inside the store is absolutely beautiful and the merchandise is all about casual American elegance. 

Next– enjoy an afternoon of more luxury shopping.

The Magnificent Mile

First, check out the shops along Chicago’s Magnificent Mile. The Magnificent Mile is a 13-block stretch of North Michigan Avenue that runs from the Chicago River to Oak Street.

It is downtown Chicago’s main commercial district, with more than 450 stores, 275 restaurants, and 70 hotels.

The high-end shops on the Magnificent Mile include:

900 N. Michigan Avenue

900 N. Michigan Avenue in Chicago also has excellent luxury shopping. Don’t miss shopping at these high-end stores:

Discover Local Businesses

Once you’ve shopped your favorite luxury stores in Chicago, it’s time to hit up some local businesses on your walk back to the hotel.

Colores Mexicanos Chicago is a colorful and vibrant gift shop full of treasures made by Mexican artisans. The store works in fair trade with families in 12 states across Mexico.

The interior of a Mexican art store in Chicago filled with colorful figurines, decorations and other goods.

If you need a pick-me up snack after all of that shopping, Garrett Popcorn Shops is a Chicago institution. Garrett Popcorn Shops was founded in Chicago in 1949, and makes small-batch gourmet popcorn. I tried the CheeseCorn and it was absolutely delicious!

Late Afternoon or Early Evening 

Walk back to The Langham, Chicago to take a break and get ready for your evening out in Chicago.

Dinner

On your first evening in Chicago, have dinner at Gibson’s Bar & Steakhouse (1028 North Rush St., Chicago, IL 60611). It’s about a 20-minute walk from The Langham, Chicago or a quick Uber ride. 

Gibson’s is an American steakhouse that opened in Chicago in 1989. Gibson’s is extremely popular, and for good reason. You’ll definitely want to make a reservation. 

The menu has American classics, including wedge salads, oysters on the half-shell, prime rib dip sandwiches and many different cuts of steak. 

I was craving something a bit casual. So, I ordered a wedge salad to share with my friend, followed by the filet sliders and fries. It was all excellent. 

Gibson’s is also famous for its huge shareable desserts.

A green, bue and white neon sign that says "Bar Gibsons Steak-Fish".
A wedge salad with romaine lettuce, tomatoes, bacon and blue cheese on a white plate.
3 mini hamburgers on a plate with a large portion of french fries and a dish of ketchup.

After-Dinner Drinks

Once you finish dinner, walk over to Pops For Champagne (601 N State St., Chicago, IL 60610). 

Pops For Champagne is an elegant champagne bar in downtown Chicago. You can order champagne by the glass, or bottles of bubbly.

A woman's hand holding a glass of champagne in front of a large wine fridge.
Brunette woman in a cream sweater dress standing in a wine bar while holding a glass of champagne.

Nighttime

It’s been a long day of exploring downtown Chicago. Now, walk back to The Langham, Chicago, and don’t forget to admire the glittering Chicago skyline on the way. 

Then, get a good night’s sleep, so you’ll be refreshed for day two of your three days in Chicago.

Day 2 (Chicago 3 Day Itinerary)

Day two of your Chicago itinerary is all about pampering. You’ll have a leisurely brunch, check out some luxury shops, and then relax at one of Chicago’s top spas. You’ll wrap up your day with dinner at your hotel, followed by a night at the theater.

Breakfast/Brunch

Start your day off with brunch at the beautiful Somerset restaurant in the Viceroy Chicago hotel (1112 N State St., Chicago, IL 60610). 

The restaurant is in the upscale Gold Coast neighborhood of Chicago. It’s about a 20-minute walk from The Langham, Chicago hotel or a quick Uber ride.

This restaurant has eye-catching blue and gold decor. You’ll definitely want to linger over your lattes and omelets! 

Smiling brunette woman standing in an upscale restaurant and holding a blue coffee cup.
Smiling brunette woman sitting in a blue leather restaurant booth while holding a blue mug of coffee

Morning 

After brunch, walk over to Oak Street for more of Chicago’s best luxury shopping. Oak Street’s high-end stores include:

A beige exterior storefront that has a Prada sign over the door.
Two high-end storefronts: a beige Chanel storefront with a large window and a black and gold Van Cleef & Arpels store.

Afternoon

Once you’re done shopping, walk a few minutes to the iconic Waldorf Astoria Chicago hotel (11 E Walton St., Chicago, IL).

First, enjoy your favorite spa service at the Waldorf Astoria Spa & Health Club. The spa is known for its fabulous spa treatments and luxurious facilities. 

I had an excellent 60-minute Waldorf Signature Massage. My massage therapist was extremely skilled and knowledgeable. The spa has a comprehensive menu that also includes facials, waxing, body treatments, nail services and more.

If you book a 60- or 90-minute service, you’re able to use the spa amenities, which include a heated lap pool, Jacuzzi, steam room, sauna, and gym. 

After your spa services, get ready for the rest of your day in the locker room. The spa has complimentary luxury toiletries that you can use, including Balmain Hair Couture products.

Lunch

Next, head to the third floor of the Waldorf Astoria Chicago for a late lunch at Brass Tack (11 E Walton St., Chicago, IL). Brass Tack is a brasserie that serves American fare with locally-sourced ingredients from the Midwest.

The interior of the high end restaurant Brass Tack, with black leather booth, and tan leather stools at the bar.
A green salad in a white bowl and coffee in a clear glass mug. Both are on the table in a restaurant.

Late Afternoon

Take a leisurely walk from the Gold Coast back to The Langham, Chicago. On the way, admire the beautiful Chicago architecture and stroll along part of the Chicago Riverwalk, a 1.25-mile-long walking path along the Chicago River. Be prepared for excellent views of downtown Chicago.

When you get back to your hotel, take a rest and then get ready for dinner.

Dinner

Have an early dinner at Travelle, the restaurant at The Langham, Chicago (330 North Wabash Ave., Chicago, IL 60611). 

The restaurant serves seasonal American cuisine in a gilded and glamorous setting. My table had great views of Marina City, aka Chicago’s iconic “corn cob” towers.

Travelle has a glassed-in kitchen, so you can watch the chef and their team at work. I ordered the burrata appetizer, and my friend’s salmon entree was the standout entree. 

A brunette woman in a cream dress. She is holding a glass of wine while sitting at a restaurant table next to a large window.
Two women's hands holding glasses of red wine in front of a display of wine bottles.

Evening

Don’t linger too long at dinner, you’re catching a Broadway show tonight at one of Chicago’s iconic theaters.

I saw “Wicked” performed at the James N. Nederlander Theater (24 W Randolph St., Chicago, IL 60601). I’m a huge musical theater fan, and it was a top-notch performance.

The James N. Nederlander Theater is also a stunningly beautiful venue. It was built in 1926 and originally was one of Chicago’s motion picture palaces. It has an incredibly ornate interior; you’ll definitely want to snap some photos inside. 

After the show, walk past the iconic Chicago Theater to see its famous glittering facade. 

A lit up gold marquee with a white witch whispering into a green witches's ear. The sign reads "the untold true story of the Witches of OZ - Wicked"
An orange and red theater marquee that reads "Theater Chicago"

 

Late Night

Grab a nightcap at The Drifter (676-8 N Orleans St., Chicago, IL 60654), before heading back to the hotel for some rest.

Day 3 (Chicago 3 Day Itinerary)

Wake up and get ready for your last day in Chicago. Check out of The Langham, Chicago hotel, and have the concierge store your bags.

Day three is all about exploring Chicago’s most famous museum and park. You’ll then shop at Chicago’s best outlet mall and enjoy a high-end seafood dinner before you head home.

Breakfast

Walk over to Starbucks Reserve Chicago Roastery for coffee and breakfast (646 Michigan Ave., Chicago, IL 60611). It’s about a 10-minute walk from The Langham, Chicago.

This is not your average grab and go Starbucks. You’ll want to linger and explore its 5 floors! At 35,000 square feet, Starbucks Reserve Chicago Roastery is the largest Starbucks in the world.

It’s a true coffee lover’s experience, and the menu and ingredients are different from your typical Starbucks. You can even order coffee flights, coffee cocktails and specialty bakery items. 

The space is immersive and unique with a curving escalator, and there’s also a rooftop where you can enjoy your coffee with Chicago city views.

A woman's hand holding a disposible coffee cup against a Chicago city skyline view.
The gold and green interior of a coffee shop.

Morning

After breakfast, head over to the Art Institute of Chicago (ARTIC). It’s about a 22-minute walk from Starbucks Reserve Chicago Roastery, or a 6-minute Uber. 

Not only is ARTIC one of Chicago’s top museums, but it’s also one of the best museums in America. If you put one museum on your Chicago itinerary, it should be this one. 

ARTIC is home to world famous works of art, including:

The museum’s collection is huge, so give yourself time to explore the museum. At a minimum, you’ll need two hours to explore the highlights of their collection.

A room in a museum with painting in gilded frames against a blue wall, and a marble bust of a woman in the foreground.
A painting called American Gothic in a museum of a serious looking woman and an older man holding in a pitchfork.

Lunch

After the museum, walk a few minutes down the street to Cindy’s Rooftop at the Chicago Athletic Association Hotel for lunch (12 S Michigan Ave., Chicago, IL 60603). Cindy’s Rooftop is known for its epic view of Chicago’s Millennium Park, including “The Bean” (an art installation by Anish Kapoor that is officially named “Cloud Gate”). 

Cindy’s Rooftop is extremely popular, so reservations are highly recommended. 

As smiling brunette woman wearing blue jeans and a tan and white checked sweater vest. She is holding a pink cocktail while standing at a rooftop cocktail bar .
Two women's hands clinking together pink cocktails on a rooftop bar with a view of an urban park below.

Early Afternoon 

After lunch, walk down into Millennium Park. You’ll want to see “The Bean” up close and snap a photo, of course. 

Millennium Park is a major gathering place and public space for Chicago residents. It has fountains, gardens and other public artworks to enjoy. There are often free events in Millennium Park, like ice skating in the winter months and a rock climbing wall, that you should be on the lookout for as well. 

Mid-Afternoon

Walk about 11-minutes back to The Langham, Chicago to grab your luggage. Then, hop into an Uber to the Fashion Outlets of Chicago (5220 Fashion Outlets Way, Rosemont, IL 60018).

This outlet mall is five minutes away from Chicago O’Hare Airport, and a great final stop on your Chicago itinerary. 

You can check your luggage at the concierge desk to make it easier to shop too.

Some of the luxury stores at the Fashion Outlets of Chicago include:

Dinner

Head across the road to Truluck’s Stone Crab Lounge (9860 Berwyn Ave., Rosemont, IL 60018). This is the final stop on your Chicago 3-day itinerary before you head to the airport. 

The restaurant is about a 10-minute walk from the Fashion Outlets of Chicago, or you can take a very quick Uber. 

Truluck’s is a traditional seafood restaurant with an elegant atmosphere. The menu features dishes like crab cakes, stone crab claws and miso-glazed sea bass. 

Truluck’s does have a dress code, so don’t show up in athletic wear or anything too casual, baggy or revealing. I wore jeans and a sweater, which was totally acceptable.

A white plate with a crab cake, half a lemon and a small silver pitcher of tartar sauce on it.
An elegant restaurant dining room with a large crystal chandelier, and white table cloths and red roses on each table.

Evening

It’s time to head home. If you’re flying out of O’Hare, you can grab a five-minute Uber to the airport from Truluck’s. 

No judgment if you fall asleep on your flight. This has been a whirlwind luxury tour of Chicago!

Other Chicago Attractions

If you decide that three days in Chicago isn’t enough, these are some other attractions to explore if you stay an extra day or two:

Other Chicago Restaurants 

Some other drinking and dining options include: 

A brunette woman wearing a black top and jeans standing in front of an ornate beige stone building.

Conclusion: 3-Day Chicago Itinerary  

That wraps up the best three-day Chicago itinerary for luxury travelers. It is a world-class city and there is so much to see and do. But you can cover a lot of ground with only three days in Chicago. 

If you’re a luxury traveler looking to explore a new city, Chicago should be your next trip. It has exceptional luxury hotels, dining, shopping, theater and sightseeing. 

Have any questions about this Chicago 3-day itinerary? Drop them in the comments!

P.S. If you’re looking for spots to take the best photos in Chicago, check out my Chicago photo guide here.

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