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7-Day Midwest Golf and Gambling Adventure

Viewed by 128 travelers

Day 1: Golfing in Chicago

Chicago, Illinois

7:30 AM

Breakfast at Wildberry Pancakes and Cafe

Start your day with a delicious pancake breakfast at Wildberry, known for its creative brunch dishes and vast selection of pancakes.
Located in downtown Chicago, easily accessible.
USD 15, 1 hour

9:00 AM

Golf at Cog Hill Golf & Country Club

Play a round at one of the top-rated golf courses in Chicago, Cog Hill, which features the famous Dubsdread course.
Drive approximately 30 minutes southwest of downtown Chicago.
USD 140, 4 hours

1:30 PM

Lunch at The Barn Steakhouse

Enjoy a hearty lunch featuring expertly cooked steaks in an elegant setting at The Barn, located near the golf course.
Less than 10 minutes from Cog Hill.
USD 40, 1.5 hours

3:00 PM

Visit Rivers Casino

Spend the afternoon trying your luck at Rivers Casino, offering poker, slots, and table games with great views of the Chicago skyline.
Head back towards Chicago, around 30 minutes from the restaurant.
Variable, 3 hours

6:30 PM

Dinner at Portillo's

Relish in a classic Chicago-style dinner at Portillo's, famous for its Italian beef sandwiches and hot dogs.
Short drive to one of their several locations.
USD 20, 1.5 hours
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Day 2: Chicago's Nightlife and More Golf

Chicago, Illinois

8:00 AM

Breakfast at Lou Mitchell's

Fuel up with a traditional American breakfast at Lou Mitchell's, an iconic diner known for its fluffy pancakes and homemade pastries.
Located close to the Loop, accessible via car.
USD 15, 1 hour

9:30 AM

Golf at Lincoln Park Golf Course

Enjoy a leisurely round of golf at this public course right in the heart of the city, with scenic views of the skyline.
Drive about 15 minutes north to Lincoln Park.
USD 50, 3 hours

1:00 PM

Lunch at The Publican

Savor a unique lunch at The Publican, a gastro-pub famous for its farm-to-table cuisine and extensive beer list.
Short drive back towards the West Loop.
USD 40, 1.5 hours

3:00 PM

Afternoon at Grand Victoria Casino

Try your hand at gaming at the luxurious Grand Victoria Casino, offering a variety of table games and slots.
Drive approximately 40 minutes from Chicago.
Variable, 3 hours

7:00 PM

Dinner at Lawry's The Prime Rib

Indulge in a sumptuous dinner with a classic menu featuring prime rib and elegant service at this iconic steakhouse.
Return to downtown Chicago, about 40 minutes.
USD 75, 2 hours
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Day 3: Golfing in Madison

Madison, Wisconsin

8:00 AM

Breakfast at Marigold Kitchen

Start your day with fresh, local flavors at Marigold Kitchen, known for its creative breakfast dishes and friendly service.
Drive approximately 2.5 hours northwest to Madison.
USD 15, 1 hour

9:30 AM

Golf at University Ridge Golf Course

Experience a challenging round at University Ridge, designed by famed architect Robert Trent Jones Jr., with scenic Wisconsin landscapes.
Short drive from Marigold Kitchen.
USD 100, 4 hours

1:30 PM

Lunch at The Old Fashioned

Savor a delicious lunch featuring Wisconsin cheese curds and bratwurst at The Old Fashioned, celebrating local flavors.
Less than 10 minutes from the golf course.
USD 30, 1.5 hours

3:00 PM

Visit Ho-Chunk Gaming Madison

Try your luck at Ho-Chunk Gaming, one of the largest casinos in Wisconsin, with a variety of gaming options.
Just a 15-minute drive from the restaurant.
Variable, 3 hours

6:30 PM

Dinner at Graze

Enjoy a downtown view while partaking in farm-fresh dishes, emphasizing local ingredients in a casual setting at Graze.
Back in the heart of Madison, a 10-minute drive.
USD 40, 1.5 hours
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Day 4: Milwaukee Casino and Golf

Milwaukee, Wisconsin

8:00 AM

Breakfast at Blue's Egg

Dive into a delightful breakfast at Blue's Egg, offering creative twists on classic dishes and using local ingredients.
Drive 1.5 hours southeast to Milwaukee.
USD 20, 1 hour

9:30 AM

Golf at Milwaukee County Parks Course

Enjoy a peaceful round at one of Milwaukee's top public courses, featuring stunning landscapes and great shot variation.
About 20 minutes from Blue's Egg.
USD 50, 4 hours

1:30 PM

Lunch at Milwaukee Ale House

Unwind after your game with a hearty meal at the Milwaukee Ale House, featuring regional beers and mouthwatering burgers.
Short drive to the waterfront.
USD 30, 1.5 hours

3:00 PM

Afternoon at Potawatomi Hotel & Casino

Hit the gaming floor at the Potawatomi, well-known for its casinos and wide array of gaming offerings.
Drive approximately 10 minutes from lunch.
Variable, 3 hours

6:30 PM

Dinner at Mason Street Grill

Experience upscale dining at Mason Street Grill, which offers steak and seafood dishes with a fine wine selection.
Return downtown, a 10-minute drive.
USD 75, 2 hours
Find Hotels in Milwaukee

Day 5: South Bend Sports Betting

South Bend, Indiana

8:00 AM

Breakfast at The Breakfast Club

Start with a classic breakfast at The Breakfast Club, a local favorite known for its eggs and pancakes.
Drive 1.5 hours south to South Bend.
USD 15, 1 hour

9:30 AM

Golf at Blackthorn Golf Club

Prepare for a rewarding round at Blackthorn Golf Club, acclaimed for its challenging layout and beautiful scenery.
Short drive from the Breakfast Club.
USD 70, 4 hours

1:30 PM

Lunch at LaSalle Grill

Enjoy upscale dining at LaSalle Grill, known for their steak and fresh-ground beef burgers, with a lovely atmosphere.
A short drive back to downtown South Bend.
USD 40, 1.5 hours

3:00 PM

Visit Four Winds Casino

Experience the fun of Four Winds Casino, providing a vibrant atmosphere, poker, and various gaming options.
About 15 minutes from the restaurant.
Variable, 3 hours

6:30 PM

Dinner at The Carriage House Dining Room

Conclude your day with dinner at The Carriage House, where the cozy ambiance complements their exquisite menu.
A short drive from the casino.
USD 50, 2 hours
Find Hotels in South Bend

Day 6: Golfing in Indianapolis

Indianapolis, Indiana

8:00 AM

Breakfast at Café Patachou

Savor a delicious breakfast of local ingredients at Café Patachou, famed for their breakfast classics.
Drive 2 hours southeast to Indianapolis.
USD 15, 1 hour

9:30 AM

Golf at Brickyard Crossing

Play a round at Brickyard Crossing Golf Course, uniquely located near the Indianapolis Motor Speedway, offering stunning views and challenges.
Short drive from breakfast.
USD 100, 4 hours

1:30 PM

Lunch at St. Elmo Steak House

Treat yourself to lunch at the legendary St. Elmo Steak House, famous for its shrimp cocktail and premium steaks.
A quick drive back towards downtown.
USD 75, 1.5 hours

3:00 PM

Visit Hollywood Casino Indianapolis

Try your luck at Hollywood Casino, offering an exciting array of games and buzzing atmosphere.
A short drive from lunch.
Variable, 3 hours

6:30 PM

Dinner at The Capital Grille

Indulge in upscale dining at The Capital Grille, known for its dry-aged steaks and an extensive wine list.
Drive back towards downtown, about 20 minutes.
USD 85, 2 hours
Find Hotels in Indianapolis

Day 7: Final Stop in St. Louis

St. Louis, Missouri

8:00 AM

Breakfast at Rooster

Delight in a delicious breakfast at Rooster, known for their crepes and breakfast sandwiches with locally sourced ingredients.
Drive 3 hours southwest to St. Louis.
USD 15, 1 hour

9:30 AM

Golf at Forest Park Golf Course

Enjoy a round at one of America’s oldest municipal courses, located in the beautiful Forest Park with challenging holes.
Short drive from breakfast.
USD 50, 4 hours

1:30 PM

Lunch at Pappy's Smokehouse

Graze on some of the best Memphis-style barbecue in St. Louis at the famous Pappy's Smokehouse.
A quick drive from the golf course.
USD 25, 1.5 hours

3:00 PM

Visit Lumiere Place Casino

Spend your final afternoon at Lumiere Place Casino, offering a variety of gaming experiences amidst a lively atmosphere.
Just a short drive from lunch.
Variable, 3 hours

6:30 PM

Dinner at Tony's St. Louis

Experience upscale Italian cuisine at Tony's, with a perfect setting to conclude your Midwest tour.
Short drive back toward downtown St. Louis.
USD 50, 2 hours
Find Hotels in St. Louis
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