A Weekend Trip to Chicago

The Bean at Chicago

It's time to pack your bags and bust out your windbreaker because we're going to Chicago, also known as the “windy city.” Located along the shores of Lake Michigan, Chicago is known for its vibrant arts scene, numerous cultural attractions, excellent shopping, and interesting architecture.

I’ve been to Chicago with close friends, for a bachelorette party, and even more recently my one-year wedding anniversary. If you plan on booking a trip soon, the perfect time to go is in the summer or on Labor Day Weekend.


How to explore Chicago:

1. Walk

  • You'll find the most beauty just by walking around and exploring the city


2. Bike

  • Divvy Bike Share (similar to CoGo in Columbus)

  • $7 for a 24-hour pass (unlimited 30-minute trips)

  • Take a bike along the beach and Navy Pier. It's the best money you'll spend with transportation


3. Taxi, Lyft, or Uber

  • The more friends you have the cheaper the taxi fare will be on your pockets

  • To save money, save the ride-share for night time activities


4. Kayak or Paddle Board

  • This is a great way to beat the traffic and explore the city from a different point of view

  • Kayak Chicago is a good place to start for pricing

Free things to do in Chicago

  • Visit the Bean in Millennium Park

  • Walk along Navy Pier

  • Go to Buckingham Memorial Fountain (Landmark in Grant Park)

  • Go to the beach!

  • Walk around downtown Chicago

  • Visit a neighborhood

  • Lincoln Park Zoo

  • Check out what events and festivals are going on while you're in town!

If you ever visit Chicago during Labor Day weekend, you'll be in awe of all the beautiful weddings that take place around the city. All the brides looked so beautiful and the grooms looked great too.

Clubs, Bars, and Lounges in Chicago

1. The Signature Lounge/Room

  • 95th Floor of the John Hancock Building

  • One of the best views of the city

  • TIP: Go to the women's bathroom for a special surprise view!

2. Untitled

  • Best Whiskey Bar in Chicago

  • Music: Hip-Hop, R&B, Jay-Z, and Justin Timberlake Mix

3. The Underground Chicago

  • Open till 5 A.M.

  • Hang-out spot for Chicago Cubs players and out-of-town celebrities

  • Dress Code Required (heels for ladies)

4. Studio Paris Night Club on Hubbard Street

  • Great DJ for all crowds

  • Nice venue + No Charge (for ladies)

  • Open till 2 A.M

5. Debonair Social Club (Wicker Park)

  • $5.00 entry fee (varies)

  • Great DJ - Top 40, Hip-Hop, and Pop

6. Crocodile Lounge (Wicker Park)

  • 90's Throwback, R&B, Pop, and Hip-Hop

7. The Godfrey Hotel - Rooftop Bar & Lounge

  • Arrive earlier than later

  • Happy Hour or Pre-Game Venue


Great neighborhoods to bar hop:
1. Wicker Park
2. Hubbard Street (Downtown)
3. Wrigleyville

Rooftop Restaurants and Brunch Spots:

Chicago Tips:

  • Stay with a friend who lives in Chicago or split a hotel with friends

  • Always eat brunch!

  • Eat at BYOB spots or bring miniatures in your purse.

  • Stay in the city (Central Loop) if you can!

  • Utilize a CashApp, Venmo, or quick pay feature to split the bills

  • Bring $15.00 for tolls (if you plan on driving from Columbus, Ohio)

  • Create a bucket list for all the things you want to do when you visit

  • Sing a lot of Beyonce' while you're on the road!

  • Buy liquor before you leave Ohio so you can drink in your hotel before you go out

  • Jump in Lake Michigan!

  • Get Giordano's Pizza to go

  • Buy a bag or tin of Garrett's Popcorn!

  • Take/Save $300.00-350.00

  • Look up hotels a month or two in advance for the best deals

Giordano's pizza
TravelsMorgan Pelt