Sample Itinerary

Every trip is customized to your preferred travel dates, length of stay, and sightseeing interests. The itineraries below are examples.

Sample Itinerary - Option 1: Complete All-Star Week Getaway

• July 9: Arrive in Chicago, check into your hotel, and enjoy an evening in River North or along the Chicago Riverwalk
• July 10: Explore downtown Chicago and attend an eligible All-Star Week activity, subject to the official schedule and ticket availability
• July 11: Visit Chicago museums, the lakefront, or another eligible All-Star Week experience
• July 12: Enjoy Chicago sightseeing and attend the Home Run Derby, if selected and confirmed
• July 13: Attend the 2027 MLB All-Star Game at Wrigley Field
• July 14: Depart Chicago or extend your Midwest vacation

Sample Itinerary - Option 2: All-Star Game City Stay

• July 11: Arrive in Chicago and check into your hotel
• July 12: Explore Millennium Park, the Chicago Riverwalk, or Navy Pier; add the Home Run Derby if selected and confirmed
• July 13: Experience Wrigleyville before attending the 2027 MLB All-Star Game at Wrigley Field
• July 14: Depart Chicago or add another hotel night

Optional Add-Ons

Personalize your sports travel experience with a few carefully selected upgrades.

Transportation

• Roundtrip airfare
• Private airport, hotel, or game-day transfers
• Rental-car reservations

Sports Experience Upgrades

• Premium, club-level, or suite seating
• Pregame hospitality opportunities
• Additional sporting event tickets

Destination Experiences

• Chicago architecture, lakefront, or neighborhood sightseeing
• Museums, dining, comedy, and entertainment experiences
• Milwaukee, Lake Michigan, or Midwest extensions

Vacation Extensions

• Additional hotel nights
• Nearby destination extension
• Travel protection options

⚾ Destination Guide: Chicago

Chicago combines world-class sports, lakefront scenery, landmark architecture, distinctive neighborhoods, museums, shopping, music, and celebrated dining. Downtown attractions and Wrigleyville can be connected by public transportation, making the city well suited for a customized All-Star baseball getaway.

Wrigley Field

Wrigley Field opened in 1914 and is one of Major League Baseball's two oldest active ballparks. Known as the Friendly Confines, it is celebrated for its ivy-covered outfield walls, hand-operated center-field scoreboard, iconic red marquee, and location in the heart of Wrigleyville. Transportation, entry requirements, and ballpark policies should be reviewed shortly before event day because operating details may change.

Top Chicago Experiences

• 🏙️ Millennium Park: See Cloud Gate, landscaped gardens, public art, and seasonal programming near the lakefront.
• 🚤 Chicago Architecture Cruise: View the city's celebrated skyline and learn about its architectural history from the Chicago River.
• 🌊 Chicago Riverwalk: Enjoy waterfront paths, restaurants, public art, and downtown views along the river.
• 🎡 Navy Pier: Explore lakefront attractions, dining, cruises, entertainment, and views of Lake Michigan.
• 🖼️ Art Institute of Chicago: Discover an internationally recognized collection spanning centuries and cultures.
• 🏛️ Museum Campus: Visit the Field Museum, Shedd Aquarium, and Adler Planetarium near the lakefront.
• 🌳 Lincoln Park: Explore green spaces, the lakefront, Lincoln Park Zoo, restaurants, and neighborhood attractions.
• 🎷 Chicago Music & Entertainment: Add blues, jazz, theater, comedy, or live music to your stay.

Food and Drink

• Chicago-style deep-dish and tavern-style pizza
• Chicago-style hot dogs and Italian beef sandwiches
• Steakhouses, chef-driven restaurants, and neighborhood dining
• Polish, Mexican, Italian, Chinese, Indian, and other international cuisines
• Local breweries, cocktail bars, rooftop venues, and classic neighborhood establishments

Where to Stay

• Wrigleyville and Lakeview: Convenient for Wrigley Field, neighborhood restaurants, and nightlife
• River North: Central access to restaurants, nightlife, galleries, and the Chicago River
• The Loop: Convenient for Millennium Park, museums, theaters, architecture, and public transportation
• Magnificent Mile and Streeterville: Shopping, dining, lakefront attractions, and hotel choices
• West Loop: Acclaimed restaurants, nightlife, and access to downtown

Weather and Packing

July in Chicago is typically warm and can be humid, with changing lakefront conditions and the possibility of summer rain. Pack lightweight layers, comfortable walking shoes, sun protection, and a light rain jacket. Check the current forecast and Wrigley Field bag policy before departure.

Getting Around

Depending on your hotel, downtown attractions may be reached by walking, Chicago Transit Authority trains and buses, rideshare, taxi, or prearranged private transportation. The CTA Red Line serves the Addison station near Wrigley Field. Allow additional time on event day and confirm the latest transportation schedules before leaving for the ballpark.