Chicago Multi-Sport Road Trips for 2026-2027

Chicago is one of the best cities in North America for a multi-sport road trip. Home to the Chicago Bears, Chicago Blackhawks, Chicago Bulls, Chicago Cubs, and Chicago White Sox, the city gives sports fans countless opportunities to experience multiple games during a single visit. Whether you're combining NFL and NHL action in the fall, adding baseball during September, or catching a same-day doubleheader, few destinations offer the variety and atmosphere of Chicago.

The 2026-2027 schedules create four outstanding weekends to pair Bears football with Blackhawks hockey, including a rare same-day doubleheader in December, a Thursday Night Football weekend in October, and an Original Six matchup against the Boston Bruins on New Year's Day. With Soldier Field, United Center, Wrigley Field, and Rate Field all easily accessible from downtown, planning a multi-sport itinerary is surprisingly straightforward.

Beyond the games, Chicago offers everything you could want from a sports getaway. Spend your time exploring Millennium Park, the Riverwalk, Navy Pier, and the Magnificent Mile before enjoying deep-dish pizza, Chicago-style hot dogs, Italian beef, and some of the country's best steakhouses. Whether it's your first visit or your tenth, Chicago delivers one of the most complete sports travel experiences in the United States.

In this guide, we'll highlight the best Chicago multi-sport weekends, where to stay, how to get around the city, and tips for planning the perfect sports getaway.

Why Chicago Is One of the Best Multi-Sport Road Trip Destinations

Few cities can match Chicago when it comes to the variety of professional sports available in a single weekend. Home to the Chicago Bears, Chicago Blackhawks, Chicago Bulls, Chicago Cubs, and Chicago White Sox, fans can experience football, hockey, basketball, and baseball without changing cities. Throughout the year, overlapping schedules create numerous opportunities to attend two or even three professional games during one trip.

Chicago is also remarkably easy to explore. Staying downtown puts you within easy reach of Soldier Field, United Center, Wrigley Field, and Rate Field using the CTA, rideshare services, or a short drive. Instead of spending your weekend traveling between venues, you can spend more time enjoying the games and everything the city has to offer.

Beyond sports, Chicago is one of America's premier travel destinations. Walk the Chicago Riverwalk, visit Millennium Park, shop along the Magnificent Mile, or explore neighborhoods like the West Loop and Wicker Park between games. Add in legendary deep-dish pizza, Chicago-style hot dogs, Italian beef, world-class steakhouses, and an outstanding craft brewery scene, and it's easy to see why Chicago remains one of the country's most popular sports getaway destinations.

Best Chicago Multi-Sport Weekends for 2026-2027

The 2026-2027 schedules create four outstanding opportunities to experience multiple Chicago teams during a single trip. Whether you're pairing Chicago Bears football with Blackhawks hockey, combining football and baseball in September, or planning around a rare same-day doubleheader, these featured weekends offer some of the best sports travel experiences of the season.

Each itinerary is designed as a two- or three-night getaway, giving you plenty of time to explore Chicago between games. Staying downtown provides easy access to Soldier Field, United Center, Rate Field, and the city's top attractions, making it simple to enjoy everything Chicago has to offer throughout your weekend.

September 19-20, 2026

Detroit Tigers at Chicago White Sox + Minnesota Vikings at Chicago Bears

Kick off the 2026-2027 season with a classic Chicago baseball and football weekend. Spend Saturday evening at Rate Field as the Chicago White Sox host the Detroit Tigers before heading to Soldier Field on Sunday for an NFC North showdown between the Chicago Bears and Minnesota Vikings. With pleasant September weather and two divisional rivalries, it's one of the best times of year to visit Chicago.

Weekend Schedule

Saturday, September 19

• Detroit Tigers at Chicago White Sox
• Venue: Rate Field
• Time: Evening

Sunday, September 20

• Minnesota Vikings at Chicago Bears
• Venue: Soldier Field
• Time: Afternoon

Why This Weekend Is Worth the Trip

This itinerary combines two of Chicago's biggest sports traditions in a single weekend. Saturday's American League Central matchup is followed by one of the NFL's longest-running rivalries as the Bears take on the Vikings at Soldier Field. Between games, you'll have time to explore the Chicago Riverwalk, Millennium Park, the Magnificent Mile, or enjoy the city's renowned dining scene before another unforgettable game day.

Recommended Package

Our Chicago Multi-Sport Road Trip Package includes game tickets, a downtown Chicago hotel, and optional flights, making it easy to experience both events with one seamless booking. Book your Chicago Bears Travel Package.

October 22-23, 2026

New England Patriots at Chicago Bears + Montreal Canadiens at Chicago Blackhawks

This two-night itinerary pairs Thursday Night Football at Soldier Field with an Original Six showdown at United Center. Watch the Chicago Bears host the New England Patriots on Thursday before returning Friday evening for the Chicago Blackhawks and Montreal Canadiens, creating one of the season's best football-and-hockey combinations.

Weekend Schedule

Thursday, October 22

• New England Patriots at Chicago Bears
• Venue: Soldier Field
• Time: Primetime (Thursday Night Football)

Friday, October 23

• Montreal Canadiens at Chicago Blackhawks
• Venue: United Center
• Time: Evening

Why This Weekend Is Worth the Trip

Few road trips offer two marquee events on back-to-back nights. Thursday Night Football always delivers an electric atmosphere at Soldier Field, while Friday's Original Six matchup between the Blackhawks and Canadiens is one of the NHL's most recognizable rivalries. The Thursday-Friday schedule also makes this an ideal getaway for fans who want to experience Chicago without committing to a full weekend away.

Recommended Package

Our Chicago Multi-Sport Road Trip Package includes game tickets, a downtown Chicago hotel, and optional flights, making it easy to enjoy both marquee events with one convenient booking. Book your Chicago Bears Thursday Night Package.

December 6, 2026

The Chicago Same-Day Doubleheader

Jacksonville Jaguars at Chicago Bears + Edmonton Oilers at Chicago Blackhawks

This is the premier multi-sport weekend on Chicago's 2026-2027 calendar. On Sunday afternoon, watch the Chicago Bears host the Jacksonville Jaguars at Soldier Field before heading to United Center that evening for the Chicago Blackhawks and Edmonton Oilers. Two major league games, two iconic venues, and one unforgettable day make this one of the best sports travel experiences of the season.

Weekend Schedule

Sunday, December 6 (Afternoon)

• Jacksonville Jaguars at Chicago Bears
• Venue: Soldier Field

Sunday, December 6 (Evening)

• Edmonton Oilers at Chicago Blackhawks
• Venue: United Center

Why This Weekend Is Worth the Trip

Same-day NFL and NHL doubleheaders are exceptionally rare, and Chicago is one of the few cities where they're realistically possible. The afternoon Bears game leaves enough time to travel across the city before puck drop, allowing fans to experience two professional sporting events in a single day without changing hotels or rushing between destinations.

The evening matchup against the Edmonton Oilers is also one of the Blackhawks' marquee home games of the season, making this an outstanding opportunity to combine NFL football with elite NHL action. If you're planning just one Chicago sports trip this season, this is the weekend to target.

Recommended Package

Our Chicago Same-Day Doubleheader Package includes Chicago Bears and Chicago Blackhawks game tickets, a downtown Chicago hotel, and optional flights, making it easy to experience one of the season's most unique sports weekends. Book your Chicago Same-Day Doubleheader Package.

January 1–3, 2027

New Year's Weekend

Boston Bruins at Chicago Blackhawks + Detroit Lions at Chicago Bears

Ring in 2027 with one of the best sports weekends on the Chicago calendar. Start the new year with an Original Six showdown between the Chicago Blackhawks and Boston Bruins on New Year's Day before wrapping up the trip with an NFC North rivalry as the Chicago Bears host the Detroit Lions at Soldier Field on Sunday.

Weekend Schedule

Friday, January 1 (New Year's Day)

• Boston Bruins at Chicago Blackhawks
• Venue: United Center
• Time: Afternoon

Sunday, January 3

• Detroit Lions at Chicago Bears
• Venue: Soldier Field
• Time: Afternoon

Why This Weekend Is Worth the Trip

Few sports weekends begin with an Original Six matchup on New Year's Day and end with a divisional NFL rivalry. The Blackhawks and Bruins have one of the NHL's most recognizable rivalries, while Bears versus Lions is always an important matchup to close the regular season. Combined with Chicago's festive holiday atmosphere, this itinerary offers an unforgettable way to start the new year.

With Saturday free to explore the city, you'll have time to experience Chicago's winter attractions, world-class dining, and iconic neighbourhoods before returning to Soldier Field for the weekend finale.

Recommended Package

Our Chicago New Year's Multi-Sport Road Trip Package includes Chicago Blackhawks and Chicago Bears game tickets, a downtown Chicago hotel, and optional flights, making it easy to celebrate the new year with two marquee sporting events. Book your Chicago Bears Travel Package.

Where to Stay in Chicago

Downtown Chicago is the best place to stay for a multi-sport road trip. The Loop, River North, Streeterville, and West Loop all provide convenient access to Soldier Field, United Center, and Rate Field while placing you close to many of the city's top attractions, restaurants, and nightlife. Whether you're walking, taking the CTA, or using rideshare services, staying downtown makes it easy to enjoy multiple games during the same trip.

If your itinerary includes a Chicago Bears game at Soldier Field, there's little advantage to staying closer to the stadium. A downtown hotel gives you easy access to all of Chicago's major sports venues while allowing you to explore the Chicago Riverwalk, Millennium Park, the Magnificent Mile, and the West Loop between games.

For visitors planning the December same-day Bears and Blackhawks doubleheader, staying in the downtown core provides the greatest flexibility for getting between Soldier Field and United Center while enjoying the city before and after each game.

Looking for the best hotel options? Explore our complete guide to Best Hotels Near United Center, where we compare the best neighbourhoods, recommended hotels, and booking tips for your Chicago sports getaway.

Should You Stay Near Soldier Field or United Center?

Although Soldier Field and United Center are located in different parts of the city, we recommend staying in downtown Chicago for almost every multi-sport road trip.

Most featured itineraries combine a Chicago Bears game at Soldier Field with a Chicago Blackhawks game at United Center or a Chicago White Sox game at Rate Field. Staying downtown gives you convenient access to all three venues while allowing you to enjoy Chicago's restaurants, attractions, and nightlife between games. Rather than changing hotels, you can easily reach each venue using the CTA, rideshare services, or a short drive.

For visitors planning the December same-day Bears and Blackhawks doubleheader, staying downtown also provides the flexibility to travel between Soldier Field and United Center without the hassle of switching accommodations.

If you're visiting Chicago for a single event, staying closer to the venue you're attending may be a convenient option. However, for anyone planning a multi-sport weekend, downtown Chicago remains the ideal home base.

Getting Around Chicago During Your Multi-Sport Road Trip

Chicago is one of the easiest major cities in North America to explore without a car. The city's extensive CTA transit system, combined with rideshare services and walkable downtown neighbourhoods, makes it simple to travel between Soldier Field, United Center, Rate Field, and many of Chicago's top attractions.

Staying downtown allows you to spend less time traveling and more time enjoying your trip. Whether you're heading to a Chicago Bears game at Soldier Field, a Chicago Blackhawks game at United Center, or exploring neighbourhoods like the West Loop and Wrigleyville, you'll find convenient transportation options throughout the city.

If you're flying in, both O'Hare International Airport and Midway International Airport provide easy access to downtown Chicago, making the city an ideal destination for a weekend sports getaway.

Related Guides:

• How to Get to United Center
• How to Get to Soldier Field

Chicago Between Games: What to Do on Your Sports Weekend

The reason the city works as a sports weekend destination is that the trip is not just the games. A weekend here that skips the food, the neighborhoods, and the walking is a wasted trip. Here is what our team recommends between the Saturday and Sunday games.

Millennium Park and Cloud Gate. The 24.5-acre downtown park anchored by Anish Kapoor's Cloud Gate sculpture (universally known as "The Bean"). Free to visit, walking distance from any Loop hotel, and one of the great American public spaces. Pair with a walk of the Chicago Riverwalk on the same morning. In summer the Jay Pritzker Pavilion hosts free concerts; in winter the McCormick Tribune Ice Rink is one of the best outdoor rinks in the country.

Deep-dish pizza. The local contribution to American cuisine. Lou Malnati's is the classic starting point for first-time visitors, with locations across the city. Pequod's Pizza in Lincoln Park is the caramelized-crust pilgrimage for locals. Gino's East and Giordano's are the two other classic institutions. Order a small deep dish per person; two is enough for four fans. Book Pequod's early on game weekends; the wait can hit two hours on Sundays.

Italian beef sandwiches. The Italian beef is the local sandwich most tourists miss. Al's Beef on Taylor Street (the original) and Portillo's (multiple downtown locations, faster service) are the two standard stops. Order it "wet" and "hot" for the full experience. Johnnie's Beef in Elmwood Park and Buona Beef are the local favorites for fans willing to travel outside downtown.

The Chicago Riverwalk and the architecture tour. The 1.25-mile Riverwalk runs along the main branch of the Chicago River from Lake Michigan to Lake Street, and connects to the Chicago Architecture Center's boat tour, which is one of the best introductions to any American city. Ninety minutes on the water, a running commentary on the buildings, and one of the great morning add-ons on a Chicago sports weekend. Book the tour a week in advance for weekend departures.

The Magnificent Mile. The Michigan Avenue shopping and hotel corridor that runs from the Chicago River north to Oak Street. Home to the Peninsula Chicago, the Drake, and dozens of flagship retail stores. In December the Magnificent Mile Lights Festival transforms the strip into one of the great American holiday walks. Worth an evening walk on any sports weekend, particularly for the New Year's weekend trip.

Fulton Market and the West Loop dining scene. The modern restaurant district, walking distance from United Center and short "L" ride from the Loop. Girl and the Goat, Au Cheval (the burger), Duck Duck Goat, Monteverde, and Roister are the standard picks. Alinea, one of the top restaurants in North America, is in nearby Lincoln Park but reservations require booking two to three months in advance. Fulton Market is the natural pre-game dinner spot for the Blackhawks weekends and the natural home base for the December 6 same-day doubleheader.

The Art Institute and the Willis Tower Skydeck. The Art Institute of Chicago on Michigan Avenue is one of the top museums in America, with permanent collections including Seurat's A Sunday on La Grande Jatte, Grant Wood's American Gothic, and Nighthawks by Edward Hopper. The Willis Tower Skydeck (the "Ledge") sits 103 floors up and offers views across four states on a clear day. Both are within walking distance of any Loop hotel and worth an afternoon between games.

Wrigleyville and Wrigley Field. The North Side neighborhood around the 1914 Cubs ballpark. Even when the Cubs are not in season, the Wrigley Field tour runs daily and the Wrigleyville bar scene is one of the most concentrated in America. Take the Red Line to Addison, walk the neighborhood, hit Murphy's Bleachers or the Cubby Bear for a beer, and eat at Salt and Smoke or Big Star for casual food. A morning walk of Wrigleyville is a strong add-on to any sports weekend.