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Weekend Guide: The Ultimate Itinerary to Chicago

We took a mother-daughter trip to Chicago!

This city is so unique and diverse. Each neighborhood has its own vibe and personality. Young or old, you will never be bored. There are some many things to see and do. If you find yourself in Chicago, use our Ultimate Itinerary to guide!! It will blow your mind. 


Some of the activities listed in this itinerary included:

  • Iconic Bars

  • Visiting the Skydeck

  • Architecture Boat Tour

  • Kayaking

  • Biking

This guide is jam-packed with amazing experiences. We included restaurants (vegan-friendly), entertainment, tours, and beaches to help you get the most out of your vacation!

*Note: You will need a car or another method of transportation to get around.



Day 1 – Rest and Recharge

• 10:00 am – Arrive: Check into hotel. • 12:00 pm - Lunch: Head to True Food Kitchen for fresh and seasonal cooking. We recommend getting the Charred Cauliflower and Ancient Grains Bowl. ($15) • 1:30 pm – Activity 1: Take a walk around your hotel. This is the best way to get to know the area you are staying in! (FREE) • 3:30 pm – Rest • 5:00 pm – Happy Hour: Drumbar sits on top of a hotel. The 18th-floor bar is lush and chic. You must visit and try their Whiskey selections. They were voted best Whiskey Bar and features award-winning cocktails! ($16)

• 7:30 pm – Dinner: For Southeast Asian food, visit Sunda. Their menu features dishes that have a Modern Asian twist. We recommend trying the Shitake Edamame Dumplings, Sweet Potato Caterpillar Roll and Sake! You can view the vegan menu here. ($18)

Total Per Person: $49 plus tax and tip

Day 2 – Sightseeing: Skydeck and Navy Pier

• 9:00 am – Activity 1: Want to see all of Chicago?! Visit The Skydeck for a fantastic view. Go out on the ledge and snap a picture. The ledge is a glass balcony that extends four feet outside the 103rd floor of Willis Tower! ($16-24)

• 11:00 am – Activity 2: Walk to the Navy Pier to catch a festival, view public art or ride a huge Ferris Wheel. This place has a little bit of everything! (FREE)  • 2:00 pm – Lunch: Eat at Chicago Diner. Voted Best Vegetarian by VegNews, this place is a must. The Taquito Fundido and award-winning Vegan Milk Shake had our mouths watering for more. ($15) • 4:00 pm – Free • 7:00 pm – Dinner: Quartino is a fantastic Italian restaurant and wine bar. Their menu features Italy’s regional specialties. If you are vegan, let your server know. They can customize any pasta dish for you. ($25)

Total Per Person: $56-64 plus tax and tip

Day 3 – Botanical Conservation and Beach

• 9:00 am – Activity 1: Garfield Park Conservatory is one of the largest and most stunning botanical conservatories in the nation. It has a swimming pool, fishing lagoon, athletic field and more! (FREE) • 12:00 pm – Lunch: Eat at The Hampton Social location in River North. The iconic “Rose all day” sign will have you taking tons of pictures! We recommend getting the Butternut Squash Toast. ($14) • 2:00 pm – Activity 2: Hit the beach! Head to Oak Street Beach to soak up the sun. It is located on North Lake Shore Drive. (FREE) • 5:00 pm – Happy Hour: Apogee is a rooftop bar that sits on the 26th-floor of the Dana Hotel. The terrace sports a colorful bar that is modern and elegant. The views of Chicago from the lounge are breathtakingWe tried the Frose (frozen Rose) and immediately felt the effects, if you know what we mean. ($10)

• 5:00 pm – Happy Hour 2: Lost Lake is a tiki bar in Logan Square that packs a major punch. Try the Twilight Gloom or Saturn in the House of Saturday Forever cocktail. All drinks come in a tiki cup or funky shaped glass. ($16)

• 7:30 pm – Dinner: Handlebar serves made-from-scratch vegetarian and vegan comfort food for breakfast, lunch, and dinner. We tried the Chili Cheese Fries, Fried Avocado Grilled Cheese, and Gyro. ($15)

Total Per Person: $55 plus tax and tip

Day 4 – Vegandale Festival and Architecture Tour

• 9:00 am – Activity 1: Vegandale is a vegan food and drink extravaganza It is a Mecca for vegans, vegetarians and the veg-curious. We tried so many different foods here. They have festivals all over the US and Canada. ($10) • 3:00 pm – Activity 2: Take a tour! Chicago has some of the best architecture in the world. We recommend booking the 75-minute Architecture Tour from Shoreline. The guide will tell you all about the skyline and famous engineers. If you can, try taking this tour at night! ($19-43)

• 7:30 pm – Dinner: Mi Tocaya is a neighborhood Mexican restaurant in Logan Square. Its colorful aesthetic and bold dishes explores the Mexican heritage of Chef Diana Davila. We recommend trying the Guacamole with Chile Ash, Salsa, Raw Cactus Salad, and Charred Butternut Squash Tacos. For drinks, order the Chicana or Paloma. ($20)

Total Per Person: $49-73 plus tax and tip

Day 5 – Lakefront Trails and Museum of Contemporary Photography

• 9:00 am – Activity 1: Take a jog on the Lakefront! The trail is 18 miles long. Run, walk or bike to your heart’s content. (FREE) • 1:00 pm – Lunch: They don't call Pick Me Up Cafe your one-stop restaurant for nothing! They offer vegan, vegetarian and meat-friendly options. We recommend getting the Vegan Benedict, Tofu Scram, and French Toast. ($15) • 3:00 pm – Activity 2: View art at the MoCP, Museum of Contemporary Photography. The institution is the best college art museum dedicated to photography. Their mission is to cultivate a deeper understanding of the artistic, cultural and political roles of photography in our world today. (FREE) • 7:30 pm – Dinner: Are you a wine, bread and olive person? Fig & Olive is for you. Embrace the magic of the Mediterranean cuisine and feast on a Forest Mushroom Crostini and Roasted Cauliflower. ($25)

Total Per Person: $40 plus tax and tip

Day 6 – Explore the Food & Drink Scene

• 9:00 am – Activity 1: For coffee, mimosas or a light bite, stop by 3 Arts Club and Cafe. The decor is very posh! ($15)

• 12:00 pm – Free • 5:00 pm – Happy Hour: London House is both a hotel and a bar. The bar potion is TWO levels. The first levels are indoors with dining. The second level has another bar with outdoor seating and stunning views of the Chicago River, Lake Michigan and the Magnificent Mile. ($15) • 7:30 pm – Dinner: Le Colonial, a Chicago famed Vietnamese restaurant, features a fantastic patio and bar. Be sure to ask for the vegan menu when you are seated. The Cha Gio Chay - crispy spring rolls, Banh Pho Xao - rice noodles with veggies, and Tau Hu Cari - tofu with veggies in yellow curry sauce are great entrees to order. ($20)

Total Per Person: $50 plus tax and tip

Day 7 – Explore the Food & Drink Scene

• 9:00 am – Activity 1: Visit the beach again! North Avenue Beach is famous for beach volleyball, dining, swimming and canoeing. (FREE)

• 12:00 pm – Activity 2: After the beach, walk or bike to Millennium Park. Grab a bite to eat on the way.  3:00 pm – Activity 3: Rent a kayak for an hour. On the lakefront trail there will be kayak vendors set up. Spend some time out on the water. ($30) • 7:30 pm – Dinner: For Latin food and great drinks, head to Ronero. The tropical, chic decor will win you over! ($20)

Total Per Person: $50 plus tax and tip

Thanks for reading this Weekend Guide to Chicago!

What recommendations do you want to try? Let me know in the comments below!

Until Next Time,


“Your life is happening now. Make it amazing!”


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