14-Day Luxury Itinerary in Chicago: Experience the Best of the Windy City

Day 1: Arrival and Explore

Chicago, USA

10:00AM

Check-in at The Peninsula Hotel

Begin your stay at one of Chicago’s most luxurious hotels, featuring a full-service spa and fine dining options.
N/A
USD500, 2 hours

12:00PM

Lunch at The Grill on the Alley

Indulge in a sophisticated atmosphere with a menu emphasizing fresh seafood and prime cuts of beef.
Short walk from hotel
USD80, 1.5 hours

2:00PM

Art Institute of Chicago

Immerse yourself in world-class art, including iconic pieces from Van Gogh and Grant Wood.
10-minute luxury vehicle transfer
USD25, 3 hours

5:00PM

Rooftop Happy Hour at Cindy's

Enjoy cocktails at this chic rooftop bar with stunning views of Millennium Park.
10-minute luxury vehicle transfer
USD50, 2 hours

7:00PM

Dinner at Alinea

Experience avant-garde cuisine at this Michelin-starred restaurant, known for its innovative tasting menus.
15-minute luxury vehicle transfer
USD300, 3 hours
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Day 2: Deep Dive into Culture

Chicago, USA

9:00AM

Breakfast at Bongo Room

Savor decadent pancakes and brunch specialties in a stylish atmosphere.
20-minute luxury vehicle transfer
USD40, 1.5 hours

11:00AM

Chicago Architecture River Cruise

Explore the city’s renowned architecture from a unique river perspective during this luxurious cruise.
10-minute luxury vehicle transfer
USD60, 1.5 hours

1:00PM

Lunch at Joe’s Seafood, Prime Steak & Stone Crab

Enjoy a sumptuous lunch featuring fresh seafood and juicy steaks.
5-minute luxury vehicle transfer
USD100, 2 hours

3:00PM

Visit the Field Museum

Discover ancient artifacts and natural history exhibits at this prestigious museum.
10-minute luxury vehicle transfer
USD40, 3 hours

6:00PM

Dinner at RPM Italian

Dine at this upscale Italian eatery known for its handmade pastas and trendy vibes.
15-minute luxury vehicle transfer
USD150, 2 hours
View Hotel Availability

Day 3: Shopping and Views

Chicago, USA

8:30AM

Breakfast at The Allis

Start the day with artisanal coffee and a breakfast plate in a chic setting.
15-minute luxury vehicle transfer
USD35, 1.5 hours

10:00AM

Shopping on Magnificent Mile

Spend the morning indulging in luxury shopping along one of the world’s most famous shopping streets.
20-minute luxury vehicle transfer
USD0, 3 hours

1:00PM

Lunch at The Signature Room

Experience lunch atop the John Hancock Center with panoramic skyline views.
10-minute luxury vehicle transfer
USD100, 2 hours

3:00PM

Visit the Skydeck

Go to the 103rd floor of the Willis Tower for breathtaking views of the city.
10-minute luxury vehicle transfer
USD30, 2 hours

5:00PM

Art & Cocktails at The Museum of Contemporary Art

Enjoy thought-provoking art exhibitions while sipping on craft cocktails.
15-minute luxury vehicle transfer
USD50, 2 hours

7:30PM

Dinner at The Capital Grille

Choose from an extensive wine list and enjoy dry-aged steaks in an elegant setting.
10-minute luxury vehicle transfer
USD200, 2.5 hours
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Day 4: Exploring Lakefront

Chicago, USA

9:00AM

Breakfast at Lou Mitchell’s

Enjoy a hearty breakfast at this iconic diner famous for its doughnuts and omelets.
20-minute luxury vehicle transfer
USD30, 1.5 hours

11:00AM

Lincoln Park Zoo

Experience a relaxing morning with nature and wildlife at this free zoo in a scenic park.
10-minute luxury vehicle transfer
USD0, 2 hours

1:00PM

Lunch at Café Ba Ba Reeba!

Savor Spanish-style tapas in a vibrant setting perfect for midday dining.
10-minute luxury vehicle transfer
USD80, 2 hours

3:00PM

Lakefront Trail Walk

Take a leisurely walk along the picturesque waterfront trail, experiencing the Chicago skyline from afar.
10-minute luxury vehicle transfer
USD0, 2 hours

5:00PM

Dinner at Geja's Café

Dine in an intimate fondue restaurant, known for its romantic ambiance and unique dishes.
10-minute luxury vehicle transfer
USD150, 2.5 hours
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Day 5: Cultural Immersion

Chicago, USA

9:00AM

Breakfast at The Pancake House

Enjoy a morning full of fluffy pancakes and breakfast classics.
15-minute luxury vehicle transfer
USD20, 1.5 hours

11:00AM

Visit the Museum of Science and Industry

Engage with interactive exhibits at one of the largest science museums in the world.
20-minute luxury vehicle transfer
USD40, 3 hours

2:00PM

Lunch at The Purple Pig

Savor Mediterranean-inspired fare in a casual yet upscale environment.
15-minute luxury vehicle transfer
USD80, 1.5 hours

4:00PM

Chicago Cultural Center

Explore the stunning architecture and historic art exhibitions in this landmark building.
15-minute luxury vehicle transfer
USD0, 2 hours

6:00PM

Dinner at Blackbird

Enjoy refined contemporary American cuisine in a chic and stylish setting.
10-minute luxury vehicle transfer
USD150, 2.5 hours
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Day 6: A Day of Relaxation

Chicago, USA

9:00AM

Breakfast at Elm Street Bakery

Start the day with artisanal pastries and freshly brewed coffee.
10-minute luxury vehicle transfer
USD25, 1 hour

10:30AM

Spa Day at The Peninsula Spa

Indulge in a luxury spa treatment, including massages and facials, to relax and rejuvenate.
N/A
USD200, 3 hours

2:00PM

Lunch at The River Roast

Dine riverside with a focus on roast meats and craft cocktails.
10-minute luxury vehicle transfer
USD75, 1.5 hours

4:00PM

Art Walk in River North

Explore Chicago’s vibrant art scene in this trendy neighborhood filled with galleries.
15-minute luxury vehicle transfer
USD0, 2 hours

7:00PM

Dinner at Swift & Sons

Savor a menu full of steaks and fresh seafood in an upscale steakhouse.
15-minute luxury vehicle transfer
USD180, 2.5 hours
View Hotel Availability

Day 7: Navy Pier & Lakefront

Chicago, USA

9:00AM

Breakfast at The Egg & I

Relish a breakfast that focuses on hearty egg dishes and fresh ingredients.
15-minute luxury vehicle transfer
USD25, 1.5 hours

10:30AM

Explore Navy Pier

Visit attractions, shops, and eateries while taking in lakefront views at this iconic spot.
15-minute luxury vehicle transfer
USD0, 3 hours

1:00PM

Lunch at Harry Caray's Tavern

Dine in a casual setting with a sports theme known for its rich menu of classic American fare.
5-minute walk
USD60, 1.5 hours

3:00PM

Boat Tour of Lake Michigan

Take in the skyline from a private boat tour on Lake Michigan, where you can relax and enjoy refreshments.
5-minute walk
USD90, 2 hours

6:00PM

Dinner at Promontory

Dine in an upscale setting focusing on seasonal ingredients and neighborhood vibes.
20-minute luxury vehicle transfer
USD120, 2 hours
View Hotel Availability

Day 8: Chicago History

Chicago, USA

8:30AM

Breakfast at Ann Sather

Enjoy cinnamon rolls and Swedish-inspired breakfast dishes in a cozy atmosphere.
15-minute luxury vehicle transfer
USD30, 1.5 hours

10:00AM

Visit Chicago History Museum

Learn about the city’s rich history through engaging exhibits and artifacts.
15-minute luxury vehicle transfer
USD25, 2.5 hours

1:00PM

Lunch at Cafe Zupas

Enjoy fresh salads, gourmet soups, and sandwiches in a casual setting.
15-minute luxury vehicle transfer
USD40, 1.5 hours

3:00PM

Visit the Chicago Botanical Garden

Stroll through stunning landscapes filled with diverse plant collections.
30-minute luxury vehicle transfer
USD15, 2.5 hours

6:00PM

Dinner at The Chicago Firehouse Restaurant

Savor classic American dishes in a historic firehouse setting.
20-minute luxury vehicle transfer
USD90, 2 hours
View Hotel Availability

Day 9: Day Trip

Chicago, USA

8:00AM

Breakfast at Hotel Cafe

Start the day with breakfast at your convenience in the hotel.
N/A
USD30, 1 hour

9:00AM

Day Trip to Oak Park

Explore the Frank Lloyd Wright Home and Studio and the art and architecture of this charming suburb.
30-minute luxury vehicle transfer
USD100, 4 hours

1:00PM

Lunch at Hemingway's Bistro

Enjoy American comfort food with a modern twist in a relaxed atmosphere.
5-minute luxury vehicle transfer
USD50, 1.5 hours

2:30PM

Visit the Oak Park Art League

Witness local artistry and exhibitions by talented local artists.
10-minute luxury vehicle transfer
USD0, 1.5 hours

4:00PM

Return to Chicago

Relax on the drive back and reflect on your day.
30-minute luxury vehicle transfer
USD0, 1 hour

5:30PM

Dinner at The Boarding House

Dine at this rooftop restaurant known for its seasonal cuisine and wine selection.
20-minute luxury vehicle transfer
USD120, 2 hours
View Hotel Availability

Day 10: Night Out

Chicago, USA

9:00AM

Breakfast at The Chicago Diner

Fuel your day with hearty breakfast options in this beloved restaurant.
20-minute luxury vehicle transfer
USD30, 1.5 hours

11:00AM

Visit the Shedd Aquarium

Explore an impressive collection of aquatic life in one of the most stunning aquariums in the world.
10-minute luxury vehicle transfer
USD40, 2.5 hours

1:30PM

Lunch at Fulton Market Kitchen

Experience a uniquely crafted menu with artful dishes in an immersive space.
20-minute luxury vehicle transfer
USD75, 2 hours

3:30PM

Rest at Hotel

Take time to relax and prepare for the evening ahead.
20-minute luxury vehicle transfer
USD0, 2 hours

6:30PM

Dinner at RPM Steak

Dine at an elegant and expansive steakhouse featuring high-quality steaks and seafood.
10-minute luxury vehicle transfer
USD200, 2.5 hours

9:00PM

Cocktails at The Aviary

End your day at this world-renowned cocktail bar, known for its creative drinks and exceptional service.
15-minute luxury vehicle transfer
USD100, 2 hours
View Hotel Availability

Day 11: Art & Architecture

Chicago, USA

9:00AM

Breakfast at Beatrix

Rejuvenate with a healthy breakfast menu featuring quality ingredients.
15-minute luxury vehicle transfer
USD30, 1.5 hours

10:30AM

Guided Art Tour

Take a private guided tour focusing on Chicago's art and architectural gems.
N/A
USD200, 3 hours

2:00PM

Lunch at The Palmer House Hilton

Indulge in a delightful finale in this historic hotel dining venue.
15-minute luxury vehicle transfer
USD75, 1.5 hours

3:30PM

Visit The Charnel House

Attend a unique theater performance or art show in this intimate venue.
15-minute luxury vehicle transfer
USD30, 2 hours

6:00PM

Dinner at Mastro's Steakhouse

Enjoy an upscale steakhouse experience with exceptional service and ambiance.
15-minute luxury vehicle transfer
USD200, 2.5 hours
View Hotel Availability

Day 12: Sports in the City

Chicago, USA

9:00AM

Breakfast at Wildberry Pancakes and Café

Enjoy an array of pancake options and breakfast classics in this cozy restaurant.
15-minute luxury vehicle transfer
USD30, 1.5 hours

11:00AM

Chicago Sports Museum

Engage with exhibits highlighting Chicago's legendary teams and sports history.
15-minute luxury vehicle transfer
USD25, 2 hours

1:00PM

Lunch at Riva Crabhouse

Enjoy fresh seafood and lakefront views while dining on the rooftop.
10-minute luxury vehicle transfer
USD120, 2 hours

3:30PM

Attend a Game

Catch a Chicago Cubs or Bulls game, while experiencing the city's enthusiastic fan culture.
20-minute luxury vehicle transfer
USD80, 3 hours

7:00PM

Dinner at The Smith

Savor classic American dishes with an urban flair in this lively restaurant.
20-minute luxury vehicle transfer
USD90, 2 hours
View Hotel Availability

Day 13: Culinary Highlights

Chicago, USA

9:00AM

Breakfast at Kane County Flea Market

Experience unique breakfast bites at this popular weekend flea market.
30-minute luxury vehicle transfer
USD40, 2 hours

11:00AM

Cooking Class at The Chopping Block

Take a luxury cooking class focusing on Chicago-style dishes with top chefs.
20-minute luxury vehicle transfer
USD150, 3 hours

2:00PM

Lunch at Quartino Ristorante

Savor Italian small plates paired with a fantastic wine list.
20-minute luxury vehicle transfer
USD75, 1.5 hours

4:00PM

Visit the Spice House

Experience a guided tour of this spice store to learn about unique flavors.
20-minute luxury vehicle transfer
USD10, 1.5 hours

7:00PM

Dinner at Topolobampo

Delight in fine Mexican cuisine with a creative twist at this award-winning restaurant.
20-minute luxury vehicle transfer
USD200, 2.5 hours
View Hotel Availability

Day 14: Final Day in Chicago

Chicago, USA

9:00AM

Breakfast at The Breakfast Club

End your trip with a relaxed breakfast, enjoying a menu filled with favorites.
10-minute luxury vehicle transfer
USD30, 1.5 hours

11:00AM

Visit Millennium Park

Stroll through the iconic Millennium Park, capturing memorable photos with ‘Cloud Gate’.
10-minute luxury vehicle transfer
USD0, 1.5 hours

1:00PM

Lunch at The Berghoff

Enjoy traditional German fare at this historic and beloved Chicago restaurant.
15-minute luxury vehicle transfer
USD60, 1.5 hours

3:00PM

Shopping at State Street

Take advantage of your last afternoon for shopping downtown at iconic storefronts.
20-minute luxury vehicle transfer
USD0, 2 hours

6:00PM

Dinner at The Signature Room at the 95th

Finish your Chicago experience with a memorable dinner and breathtaking skyline views.
15-minute luxury vehicle transfer
USD200, 2.5 hours
View Hotel Availability