A Perfect Blend of City Life and Nature: Discover Chicago

Chicago is a city that effortlessly combines the best aspects of both urban and natural settings and offers an experience that will leave your group in awe with its stunning architecture, world-class museums, and inviting sights tucked along the shores of Lake Michigan. From adventurous students seeking thrills to business visitors craving excitement, Chicago embraces all who step foot on its streets warmly.

Practical Travel Tips for Groups in Chicago

Try CityPass to make the most of your group's budget in Chicago. Seatgeek.com is the best site to look for affordable last-minute tickets to Cubs games at Wrigley Field. It also offers  more than 50% off admission to the city's major attractions. If your team includes young children that need supervision, you might not be a suitable fit for this option.

If you're looking for affordable activities for groups, Chicago offers various free events. Consult the thorough Guide to Free Activities in Chicago for more information about these fantastic possibilities. From stunning parks to fascinating museums, there are likely to be plenty of exciting activities you can attend without breaking the bank.

Parc 55 Wyndham

Just a short walk from Union Square, is perfect for adult groups wanting to experience San Francisco's culinary and nightlife scenes. The hotel's sophisticated and spacious guestrooms and public areas provide fantastic city views.

The Pickwick Hotel

The Pickwick Hotel is a beautifully restored historic property, centrally located for groups to enjoy the best of San Francisco. Adjacent to the Westfield San Francisco Centre and just blocks away from the Moscone Convention Center, it is perfect for student and adult groups attending conferences or exploring the city. The hotel offers a great atmosphere and excellent value for money.

Hotel Mark Twain

The Mark Twain hotel is a top-rated budget-friendly property in the up-and-coming Tenderloin District. Groups will enjoy its convenient location near some of the city's finest culinary gems.

Ideal Time to Visit Chicago

Find incredible group hotel discounts in Chicago during the icy winter, when the temperature regularly drops below a bone-chilling 20 degrees.

If your group wants to see the city's stunning architecture, plan your trip for late spring or early summer. When Chicago's architectural attractions peak during these seasons, you and your group can explore the city's rich history and iconic sites. If you want to fully experience it all, go on a river trip to see the beautiful skyline and hidden gems.

Don't forget to include the Willis Tower or The John Hancock Building in your agenda for an incredible bird's-eye view of the city. These towering landmarks provide breathtaking panoramic vistas, allowing you to capture picture-perfect moments and create lasting memories with your group.

Start planning your trip today and prepare for an unforgettable adventure in the heart of Chicago!

Group Travel Tips and Transportation in Chicago

Visiting Chicago with your group? Utilize the city's two convenient airports, O'Hare and Midway. The excellent train transportation choices make getting to the city center simple. Consider walking, taking the quick and convenient "L" train, or using the buses to avoid the stress of parking. This will save you time and allow you to experience the city to the fullest.

Are you traveling in the winter? Chicago boasts a vast network of underground and skywalk pathways that offer warmth and protection while you travel through the city. With these practical tunnels, you can see Chicago's wonders while remaining warm and weather-protected.

Discover the best of Chicago by making transportation choices that are both convenient and comfortable. Whether you're a tourist or a local, embracing the city's public transportation system and utilizing the well-designed winter pathways will enhance your experience and make your visit all the more enjoyable.

Top Group Dining Experiences in Chicago

Chicago offers no shortage of top-notch group dining experiences that cater to various tastes and preferences. For a classic Chicago experience, head to a renowned steakhouse like Gibson's or Chicago Cut Steakhouse, where you can savor perfectly cooked prime cuts in an upscale setting. For a lively atmosphere and diverse menu options, visit Eataly, an Italian marketplace with multiple restaurants under one roof.

If you're in the mood for a unique culinary adventure, try Alinea, a three-star Michelin restaurant that offers avant-garde dining experiences. For a more casual vibe, head to Portillo's for their famous Chicago-style hot dogs or Lou Malnati's for deep-dish pizza. Whatever your group's culinary desires, Chicago has a dining experience to satisfy every palate.

Fun Group Activities in Chicago

Embark on an architectural boat tour along the Chicago River to marvel at the city's stunning skyline. Explore Millennium Park and challenge your group to a game of frisbee or enjoy a picnic amidst iconic art installations like "The Bean."

You can also consider taking a group bike ride along Lakefront Trail or renting kayaks for a fun water adventure on Lake Michigan. For a dose of laughter, catch an improv show at Second City, known for launching comedy legends.

Best DC Hotels for Groups

Find the perfect group hotel in DC by choosing one with a great location. Access to public transportation is a must, especially during the colder months. Groople partners offer excellent customer service and can accommodate groups of any size. Here are some of our top picks.

Hampton Inn Washington Downtown Convention Center

Hampton Inn is the perfect choice for groups attending an event at the Walter E. Washington Convention Center in downtown DC. With its prime location and proximity to dining and shopping, it's an ideal base for all group activities. As an added bonus, groups can enjoy complimentary hot breakfast and WiFi, making it a valuable choice for business trips.

Metro Points Hotel 

The Metro Points Hotel is a great option for groups wanting to stay close to DC without the hustle and bustle. With a complimentary shuttle to and from the city and just one mile from the New Carrollton Metrorail Station, it's convenient for exploring. Plus, free bus parking makes it perfect for student groups on a budget.

Doubletree by Hilton Washington DC

The Doubletree by Hilton Washington, DC, is the ideal location for your corporate group. With modern and comfortable rooms, and a prime location in Dupont Circle just three miles from Ronald Reagan National Airport, it caters to even the most demanding groups. Enjoy the 15 Ria restaurant's extensive wine list and superior New American cuisine during your stay.

Group Savings in DC: Tips and Tricks

Good news, budget-conscious travelers! All the government buildings and monuments in DC are free to visit. The Smithsonian museums are also free, but prepare for long lines. To dine on a budget, head to the college areas for great eats. If visiting in winter, be sure to dress for the chilly weather to avoid paying full price for cold-weather gear.

Best Times to Travel to DC

Visit Washington DC, during Cherry Blossom season for a stunning display. April is the best time, and you can find hot spots beyond the National Mall. For budget-friendly and less crowded accommodations, plan for late August to early September. However, the Christmas holidays can be crowded with families visiting the city for shopping and holiday lights.

Getting to and around DC for Groups

DC has two airports, Dulles and Reagan, with plenty of options for groups looking to travel by air. Groups coming from the Northeast can also easily access DC by train. For charter bus travelers, hotels outside the city limits near a metro station offer convenient parking. A SmarTrip card is a great option for unlimited metro or bus travel within the city. Finally, walking is a great way to explore DC, especially with a pedestrian map on a nice day.

Group Dining in DC

Save on dining in DC by planning ahead. Ask your hotel to pack a brown bag lunch for your group, or enjoy a picnic in one of DC's many outdoor parks. Head to the restaurants near Georgetown University for affordable and varied dining options. Stretch your budget even further by purchasing local Groupons for DC restaurants.

Best DC Activities for Groups

Visit DC's best free attractions, including government buildings, monuments, and exhibits. Take advantage of the National Zoo's free admission and see the famous pandas. Spend a day or two at the Smithsonian, home to remarkable collections. Explore Rock Creek Park and its free planetarium. Don't forget to snap a group photo in front of the White House.

The Groople team is ready to help you get the best possible hotel rooms at the best rates in Washington DC. Give us a call and let’s start planning a successful group trip.

Top Things to Do/See in Washington, DC

  • Tour the US Capitol
  • Visit the Lincoln Memorial
  • Visit the National Air and Space Museum
  • Tour the Smithsonian Museums
  • Visit the National Zoo
  • See a performance at the John F. Kennedy Center
  • Visit the Library of Congress
  • Visit the National Gallery of Art
  • Dine in the Adam’s Morgan Neighborhood
  • See the Cherry Blossoms Festival in Spring

Yearly Weather Averages

The Top 10 Things to Do in Chicago

  • Explore the Art Institute of Chicago
  • Wicker Park and Logan Square.
  • Chicago Theatre or enjoy live music at the iconic House of Blues.
  • National Museum of Mexican Art
  • Chicago Riverwalk
  • Chicago Blues Museum
  • Peggy Notebaert Nature Museum
  • Adler Planetarium.
  • Chicago Bulls Basketball game
  • Garfield Park Conservatory
Month High Low
January 32° 18°
February 38° 24°
March 47° 32°
April 59° 42°
May 70° 51°
June 80° 61°
July 84° 66°
August 83° 65°
September 76° 57°
October 64° 46°
November 49° 35°
December 37° 24°
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