• Home
  • About
  • Work With Me
  • Contact
  • Nav Social Icons

  • Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
  • Skip to footer
  • 2022 Guide to Cleveland in The Winter
  • View The Blog
  • Work With Me
  • About
  • Shop My Amazon Faves
  • Mobile Menu Widgets

    Social

    Search

Local Love & Wanderlust | Cleveland-Based Travel & Lifestyle Blog

Local Love & Wanderlust | Cleveland-Based Travel & Lifestyle Blog

All Things Cleveland Ohio & Travel

  • Destinations
    • Arizona
    • California
    • Illinois
    • New York
    • Louisiana
    • Nevada
    • Ohio
    • Oregon
    • Washington
  • Guides
    • Travel Guides
    • Cleveland Ohio Guides
    • Hotel Guides
    • Itineraries
  • Cleveland
    • 2022 Guide to Cleveland in The Winter
    • Neighborhood Guides
  • Shop
    • Shop My Faves
    • Shop Photo Prints

A Birthday Weekend in Chicago

Destinations

Chicago is a short six-hour drive from Cleveland and was the perfect road trip destination to celebrate my birthday weekend. We’ve been to the Windy City a handful of times, but I was excited to get to explore even more.

Day One: Travel, Art, and Good Eats

We got on the road and head West towards Chicago from Cleveland. This is going to be one long, boring drive through a lot of flat land but the drive goes quickly.

We arrive at our hotel Kimpton’s The Grey, a hotel in the Loop that we primarily booked for the amazing and huge soaking tub but also because we love Kimpton hotels. Our room is huge and the hotel is gorgeous. I am super excited about soaking in the tub at the end of the day!

After settling in and relaxing in our hotel room, we head out to visit the Art Institute Chicago. It was an incredible museum full of classics we’d never seen in person before. Amazing and well-known works by van Gogh, Seurat, Dalí, Hokusai, Hopper, Warhol and so much more.

The Obama presidential portraits were in town in a traveling exhibit and it was really cool to see in person. Fun fact, this is also the museum that Ferris Bueller and friends visit in Ferris Bueller’s Day Off.

The Obama Presidential Portraits were in town when we visited Art Institute of Chicago
This bread was so delicious

After hours of getting our art on, we found a nearby restaurant across from Millennium Park that did not disappoint. Dinner at Acanto was a memorable, delicious, and happy last-minute discovery. On the walk back to our hotel we pass the street sign for the start of the famous Route 66, now we can say we were at the start and the end in Santa Monica. I took some photos of Chicago streets at night with my Fuji x100v, a small mirrorless camera I bought for travels since I oftentimes don’t want to lug around my Canon DSLR. Got some great, moody nighttime shots on the walk back.

Really cool street light
We’ve now been to the start and the end
I loved these flowers in the center of the streets

I ended our evening soaking in the amazing tub with my Air Pods and a book on the Kindle. A perfect way to end the day.

Day Two: Rainbow Cake, The Bean, and Boat Ride

Today is my birthday and we are on a mission to get a slice of rainbow cake. Our hotel was a short walk from Goddess And The Baker’s Wabash location. We got breakfast and I got a slice of their well-known rainbow cake, yum! We ate our breakfast while watching the L train go by on the raised tracks. As a city girl, I love these views.

It’s my birthday and I’ll eat rainbow cake if I want to

After breakfast, we make our way over to Millenium Park for an obligatory visit to Cloud Gate, or “The Bean”. It’s such a fun tourist thing to do that I don’t even mind the large groups of people. We walk around the park and get stuck in a short rainfall before we drive to Randolph Street to explore.

The Bean is always a bit dirty but fun for photos
I love this fountain

It’s time for a late lunch and we put our name on the list at Au Cheval. While waiting, we check out the sugargoat and split a chocolate chip cookie. Our wait is up and we head back to Au Cheval, a small, dimly lit diner with major ambiance and delicious burgers. Afterward, we find Jeni’s Ice Cream and we get free ice cream since it’s my birthday. We love Jeni’s!

Our next stop is to check out the shops in Lincoln Park. I find some new shops I’ve never heard of before. Some classics I love, and the always exciting finding shops for stores you’ve only ever seen online. We perused the shops on Armitage Ave to spend some time before our reservations for a sunset cruise. Some of my favorite shops we visited were top drawer, Marine Layer, Lush, Rothy’s, Gorjana, Kiehl’s, and Paper Source. Some other great shops we visited were Aesop, Allbirds, Outdoor Voices, Parachute, and All She Wrote. I could have spent a lot of time just on this street alone but we had a cruise waiting.

We get back downtown and struggle to find the parking closest to the boat we had reservations on. I had booked a Sunset Cruise through Wendella. I must not have paid attention because I thought it was an architecture cruise during sunset. However, it was actually a cruise that took us out onto Lake Michigan. Oops! It was still a lot of fun and well worth it for the views.

Chicago has an incredibly dense shoreline of buildings and skyscrapers that makes for some amazing views. The most interesting part was waiting for the locks to open. The river pours into the entrance of Lake Michigan but you have to wait for the water levels to even out.

After our cruise, we have reservations for dinner at Nonnina for my birthday dinner. We have a tasty cheese board, salads, and Italian fare and then call it a night. Tonight I soak in the huge hotel tub with a bath bomb I bought earlier at Lush. Another perfect end to the day.

Day Three: Shopping and Chicago Fare

Slept in again and have a late breakfast at Stax Cafe, a spot I heard lots of good about and we have some delicious pancakes before making our way to Chicago’s West Town neighborhood to check out Lost Girls Vintage, a shop I follow on Instagram and really wanted to check out while in town. We also check out the neighboring Paperish Mess shop that had lots of fun paper goods and accessories.

Next, we drive over to Wicker Park for more shopping. We stroll up and down N. Damen Ave and N. Milwaukee Ave and visit many of the shops. Some highlights were: Shinola where I bought a monogrammed journal and Fjällräven where I bought a new backpack. Some other notable shops were Northface, Marine Layer, Diptyque, Levi’s, and a really cool book store whose name I forgot.

The sun was out in full force so we decided to go get lunch at Portillo’s, a Chicago institution. I was not a fan, but Nathan enjoyed his. I ended up with a salad which was really good.

The hot day and shopping wore us out so we went back to the hotel for a long nap. When we woke up, we thought we would try to visit the 360 Observation Deck at the Hancock Building. Unfortunately, the tickets had sold out for the day. We decided to just get dinner and wrap up the evening so we drove out to Lou Malnati’s pizza. Sadly, it was another disappointing restaurant spot. Many told us this pizza was the best, but the crust was so hard it hurt my teeth. (I still think Giordano’s has been the best of the spots I have tried on previous visits. )

Day Four: Fish Ice Cream, Failed Beach & National Park attempts

We slept in and decided on a late breakfast at Elephant and Castle so Nathan can have an English Breakfast. After breakfast, we drive around the city to visit for a few photo ops, but a street fair prevented that.

We then tried to visit Oak Street Beach but parking was impossible so we gave up. We seem to have this problem every time we visit, so hard to get a parking space. Next time we’ll plan better. There was a shop, Taiyaki, that had cute, Instagram-able fish-shaped ice cream cones and I had to try one.

We planned on visiting Indiana Dunes National Park since it was on the drive home. Unable to find parking, we try the neighboring state park and find a spot. We did get a parking space but only took a quick walk around before getting back on the road.

Overall we had a really great time even though the end of the trip sounded like a lot of bummers. Not every trip is going to go 100% perfect, and that’s okay. It’s still fun to travel and experience somewhere new.

Find more content like this under: Destinations, Chicago, Illinois

Other Posts You Might Like

Crystal blue waters in Crescent Lake, Olympic National Park | Local Love and WanderlustVisiting Beautiful Lake Crescent in Olympic National Park
Palm Trees lining a desert oasis in Palm SpringsAndreas Canyon, An Easy Desert Hike In Palm Springs, California
Cactus and succulent plants in a greenhouseMoorten Botanical Garden & Cactarium

Reader Interactions

Comments

  1. Jazmin Marie says

    February 21, 2023 at 10:19 am

    I love the bit about having a hard time finding parking near Oak Street Beach – so true!
    You ate at some delicious locations, I haven’t tried Taiyaki yet though. Thanks for the share.

    Reply
    • Jen @ Local Love & Wanderlust says

      February 22, 2023 at 1:56 pm

      It really is so hard! haha. The ice cream is so fun, I love how the cone is basically like a fish-shaped cake 🙂 Glad you enjoyed the post.

      Reply

Leave a Reply Cancel reply

Next Post >

Local Love Journal: A Cleveland East Side Afternoon

Primary Sidebar

Behind The Blog

Hey there, I'm Jen - a photographer and designer on a mission to explore Cleveland, Ohio, and beyond, one adventure at a time! I share plenty of hiking and outdoor content, as well as thoughtful travel guides to postcard-worthy destinations, features on amazing local businesses, and insider tips for uncovering hidden gems and the best experiences in Cleveland. So glad you're here!

Learn More
Work With Me

Let's Connect

Reader Favorites

  • The Lone Cypress on the 17-Mile Drive Monterey, California
    Destinations , Guides , Outdoors Where to Stop Along the 17-Mile Drive in Monterey, California
  • Cleveland , Outdoors 5 Amazing Cleveland Metroparks You Need To Visit (Plus, What To Do & See At Each)
  • Cleveland , Guides , Photography Cleveland Script Signs & How To Find Them
  • Cleveland A Look Inside City Goods in Ohio City, One of Cleveland’s Most Unique Shopping Experiences

Disclosure

Local Love & Wanderlust is a participant in the Amazon Services LLC Associates Program, as an Amazon Associate, we earn from qualifying purchases at no extra cost to you. Read our disclosure for more details on other partnerships we have.

Follow Along

@localloveandwanderlust

🍕Slice, Slice, baby🍕 Have you checked out Cl 🍕Slice, Slice, baby🍕 Have you checked out Cleveland's newest slice shop, @geracissliceshop in Downtown?

I was out of town when they opened so I was excited to finally check them out. 

Here's what you'll find when you visit: 
🔸Tasty pizza by the slice or pie, salads, garlic pillows, meatball flights, and more.
🔸A short walk away from concert venues and sports arenas, a perfect place to grab a slice after a show or game
🔸Family Owned for 65 years 
🔸Cute outdoor patio space
🔸Retro Vibes, fun decor, and photo-ops galore
🔸Caesar Marie, your next favorite Caesar (if you know me, you know I'm always on the lookout for good Caesars)

If you've been, tell me your favorite thing on the menu in the comments ⤵️

📍603 Prospect Ave E, Cleveland, OH

#downtowncleveland #cleveland #thisiscle #clevelandfoodie #clevelandblogger 
#travelblogger #clevelandpizza #familyownedbiz #crustyourinstincts #geracissliceshop Pizza Shops in Cleveland
🔹Now Open🔹Patron Saint, a new Italian-inspir 🔹Now Open🔹Patron Saint, a new Italian-inspired all-day café + aperitivo bar in Cleveland’s Ohio City!

✨Tag a friend you’d love to visit with✨

I was so excited for the opening of this lovely cafe. The former Vitrolite Tile showroom had such unique elements you’ll see blended into the modern cafe and the food was quite good! 

This all day cafe has Italian-inspired cafe dishes paired with coffee and spritz beverages and includes an aperitivo hour at 4pm that includes some bar snacks that switch up every couple days, a perfect start to your evening or an after work treat.

Check out their website for more details on parking and menu items.

📍Located in the Hingetown part of Cleveland’s Ohio City neighborhood at 2915 Detroit Avenue, Cleveland, Ohio 

🕑 Mon-Fri 7a-8p and Sat 8a-2p
.
.
.
.
#patronsaintcle #ohiocity #hingetown #clevelandohio #thisiscle #ohiotheheartofitall #apertivobar #italianinspired #clevelandcafe #beautifulinteriors #vitrolitebuilding #clevelandblogger #travelblogger #hellofrom
POV: You visit Downtown Cleveland on a Friday nigh POV: You visit Downtown Cleveland on a Friday night 
.
.
.
#thisiscle #e4thcle #geracisliceshop #cleclothingco #downtowncleveland #ohiotheheartofitall #cleveland #ohio #clevelandblogger #traveldestination #hellofrom #beautiful_destinations #travelblogger #locallove 
@thisiscle @ohiotheheartofitall @e4thst @geracissliceshop @cleclothingco
6 epic and easy views you can see in Rocky Mountai 6 epic and easy views you can see in Rocky Mountain National Park!

✨Save for future visit✨

These epic views deliver with minimal effort because sometimes you don’t want to hike a few miles to be rewarded with breathtaking scenes.

📍Alluvial Fan: this spot has a very interesting history you can read about on site, it’s also very relaxing to listen to the rushing waters.

📍Hiking Bear Lake to Nymph Lake & beyond. It’s an easy hike depending on the season. We had partial snow so we rented spikes and poles. The views on the way up are dreamy. You can continue past Nymph to several other lakes if you’re up for it.

📍Sprague Lake is just a 30 minute drive from the park entrance and one of our favorite spots. Epic sunrises nature, and mountains-reflecting-in-water views.

📍Moraine Park is huge and within the National Park boundaries. The views are vast.

📍Driving Trail Ridge Road will take you as far as 12,000 feet above sea level 😳 with many stops along the way, this is a great way to enjoy the park. During winter it’s closed and opens gradually through mid- May once the snow melts enough. 

Intro screen: Many Parks Curve seen from Trail Ridge Road

Closing scene: View #6: 📍Glacier Creek at Prospect Canyon

Do you have a favorite view in RMNP?
.
.
.
.
#rockymountainnationalpark #rockymountain #rmnps #nationalparks #hikingtrails #abovesealevel #colorado #visitcolorado #estespark #estesparkcolorado #clevelandblogger #clevelandtravelblogger #clevelandphotographer #optoutside #exploremore #easyhikes
WEEKEND IN CLEVELAND Memorial Day Weekend Saturday WEEKEND IN CLEVELAND
Memorial Day Weekend Saturday Itinerary

{✨SAVE THIS FOR YOUR WEEKEND PLANS✨}

Heyyy It’s Memorial Day weekend so just about everything you do is going to be busy and full of people so keep that in mind as you plan. Here’s a fun Saturday itinerary to make the most of the lovely weekend in Cleveland! Let me know if this inspires your weekend 🫶

🥪 Start off with a yummy breakfast sandwich at Martha on the Fly (Sat 9a -3p) you can order yours online first for quick pickup. @marthaonthefly 

Hop in your car and drive down to Cuyahoga Valley National Park and surrounding area. @cuyahogavalleynps & @clevemetroparks Hinckley Reservation

🥾Put on your hiking boots and hike some incredible Ledges at:
➖ Virginia Kendal Ledges at Cuyahoga Valley National Park
➖ Wordens Ledges Hinckley Reservation 
➖ Whipps Ledges Hinckley Reservation 

🍪 Stop at Trail Mix Peninsula to grab a light snack and beverage while exploring the outdoors.
📍1600 West Mill Street, Peninsula, OH 44264

🌊 Head back to Cleveland and visit Edgewater Beach to enjoy some sunshine and our mini ocean Lake Erie. Grab an ice cream treat at the Beach House.
📍Edgewater Beach, Cleveland, OH 44102

Spend the evening in Ohio City: @ohiocityinc @hingetown 

🍽️ Grab dinner in the Hingetown area, a few suggestions: 
@amba_cle (4p-11p)
@saucybrewworks (11a-12a)
@bananablossomthaicuisine_cle (4p-10p)

While in the area be sure to catch Station Hope: a celebration of hope and a dialog for change performed by @cptcle . We’ve been attending for years and I highly recommend checking it out. 

⏰ 7pm-10pm
📍St. John’s Episcopal Church in Ohio City & the surrounding area - 2600 Church Ave., Cleveland, OH. 44113

Unwind after your day of adventure and experience with a tasty beverage - all these spots are nearby and offer both alcohol and non-alcohol based cocktails for everyone to enjoy 🍹
@thehangarcle (2p-12a)
@bookhousebrewing (12p-12a)
@bar_amba (4p-11p)
@jukeboxcle (11:30a-1a)

BONUS: squeeze in some shopping at City Market at @citygoodscle, the 2nd & 4th Saturday through September 11am-4pm
📍 1442 West 28th Street, Cleveland Ohio, 44113

Have fun! ✌️🫶

Footer

Privacy & Cookies: This site uses cookies. By continuing to use this website, you agree to their use.
To find out more, including how to control cookies, see here: Cookie Policy

On The Blog

  • Cleveland
  • Destinations
  • Lifestyle
  • Outdoors
  • Guides
  • Photography

Info

  • About
  • Contact
  • Privacy Policy
  • Terms of Use
  • Disclosure

Search The Blog

Copyright © 2023

 

Loading Comments...