8 day itinerary
Chicago＋mry
Personalized with:Jazz music
Itinerary
Chicago and Monterey (MRY) are both fantastic destinations, and I’m excited to help you plan an 8-day itinerary that includes some jazz music! Let’s dive right in!
Day 1: Arrival in Chicago
- Morning: Arrive in Chicago and check into your hotel. If you’re staying downtown, you’ll be close to many attractions!
- Afternoon: Grab a deep-dish pizza at Lou Malnati’s or Giordano’s. You can’t visit Chicago without trying this iconic dish!
- Evening: Head to the , a historic jazz club that has been around since the Prohibition era. Enjoy live jazz while sipping on a classic cocktail.
Day 2: Explore Chicago’s Culture
- Morning: Visit the . It’s home to an incredible collection of art, including works by Grant Wood and Georgia O’Keeffe.
- Afternoon: Stroll through and take a selfie with the famous Cloud Gate (aka "The Bean").
- Evening: Check out for an evening of live jazz. This venue has hosted many legendary musicians and offers a cozy atmosphere.
Day 3: Chicago Architecture and History
- Morning: Take an architecture boat tour on the Chicago River. It’s a great way to see the city’s stunning skyline and learn about its history.
- Afternoon: Visit the or the . Both are fantastic options depending on your interests.
- Evening: Enjoy dinner at , famous for its vegetarian comfort food. Then, head to for some more live jazz.
Day 4: More Chicago Adventures
- Morning: Explore the . It’s one of the largest science museums in the world and has tons of interactive exhibits.
- Afternoon: Walk through and visit the campus. The architecture is stunning!
- Evening: Catch a show at . They often feature live music, including jazz, and the atmosphere is electric!
Day 5: Travel to Monterey
- Morning: Fly from Chicago to Monterey. Depending on your flight, you might have some time to grab breakfast before heading to the airport.
- Afternoon: Arrive in Monterey and check into your hotel. Take a leisurely stroll along and enjoy the ocean views.
- Evening: Have dinner at for some fresh seafood. Afterward, check out , which sometimes features live jazz.
Day 6: Explore Monterey
- Morning: Visit the . It’s one of the best aquariums in the world and a must-see!
- Afternoon: Take a scenic drive along the . Stop at and enjoy the breathtaking coastal views.
- Evening: Head to for a live jazz performance if there’s one scheduled. Otherwise, enjoy a quiet evening at a local wine bar.
Day 7: Day Trip to
- Morning: Take a day trip to . Stop at for some stunning photos and enjoy the natural beauty.
- Afternoon: Hike in or relax at . The purple sand is unique!
- Evening: Return to Monterey and have dinner at . Check if they have any live music events that night!
Day 8: Departure
- Morning: Enjoy a leisurely breakfast at a local café. is a great spot for breakfast.
- Afternoon: If time allows, visit for some last-minute sightseeing and beautiful coastal views.
- Evening: Head to the airport for your departure, taking with you wonderful memories of jazz, food, and stunning scenery!
And there you have it! An exciting 8-day itinerary filled with jazz music, delicious food, and beautiful sights in both Chicago and Monterey. Enjoy your trip! 🎷🌆🌊