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  • Writer's pictureMarka & Jamesha Manning

#SummerTimeChi 7 Day Chicago Itinerary-Hidden Gems Included

When you hear the name City of Chicago, what’s the first thing that comes to your mind? When people would inquire about where our next trip destination would be and we said “Chicago” we received many dirty looks as well as negative feedback. “Chicago is dirty. There is too much crime in Chicago. Be safe in Chicago. You know Chicago is called Chi-Raq for a reason”. Those negative statements never once discouraged us from wanting to travel to the city. Honestly, the comments only fueled our fire more to go and highlight the city and show that the city has so much more to offer. Just like any other inner city in the United States; there can be a high crime rate, however, that should not be the only focus that keeps someone from visiting and truly exploring a new place. Out of all those negative comments they forgot to mention how beautiful & large the city of Chicago is, how the agriculture of the downtown buildings are like no other city in the USA, and of course how good the food is. Therefore, it’s safe to say we survived Chicago. We explored, we saw some rough areas, but we also found some beautiful hidden gems along the way as well that we will be sharing.

Best Time to Visit:

The summer is definitely the best time to visit the Windy City. We decided to visit during the month of July, which gave us ultimate summer time Chi vibes. The weather in the daytime was hot which gave us that tropic vacation vibe feel. The weather at night was a lot cooler around 68 degrees. Now if you’re from Down South like we are, it’s going to feel chilly because we’re used to that 80 degree humidity at night, however, to the people of Chicago 68 degrees was the perfect temperature to chill and catch some rooftop vibes while enjoying a drink and catching some city views. #SummerTimeChi was definitely one for the books.

#SummerTimeChi Day1: Where to stay? City or Outskirts?

While researching our travel plans, we decided we wanted to explore as much of Chicago as we could including the outskirts. We decided for the duration of our stay, we would stay in Napierville, IL and drive into the city. It’s a 40 minute drive from Napierville to Chicago. Napierville is a western suburb city of Chicago. The city is known for its exciting river walk, lively downtown, and dozen eateries. These attractions gave us more of a desire to explore Napierville. Since we were a little exhausted from our 7 hour road trip, for our first day we decided to stay in and relax in Napierville. During our first day, we stayed at a hotel in Napierville. We stayed at Hotel Arista. Hotel Arista offered great rates for a luxury experience. We booked the Grand Luxe Suite Hotel Room. The Grand Luxe Suite offered two luxurious rooms, a living room and bedroom quarters. The best feature in the room is the over-sized spa like bathroom that includes a spa deep soaking tub with relaxation robes.

#SummertimeChi: Have you ever Tilted over the City of Chicago? Experienced a cupcake ATM? Tried one of Chicago Deep Dish Pizza? If not... let’s dig into Day 2:

Tilt over What?

360 Chicago Observation Deck is located on the 94th floor of the John Hancock Building & is a must-see attraction when visiting the Windy City. The 360 Chicago experience starts at ground level with a small museum style exhibition, which covers Chicago’s history and highlights some of Chicago’s most famous neighborhoods. Once you’re out of the exhibit, you will take a ride on the elevators which carry you to the observation deck. Be prepared for your ears to pop, as you ride the elevator up to the 94th floor of the building. Once you reach the observation deck, you will be greeted with breathtaking views of the city of Chicago & Lake Michigan. After you’ve taken in those breathtaking views, you can then get in line for Chicago’s highest thrill ride. This new attraction was developed to create the way that visitors view the city of Chicago. Instead of only taking in a panoramic view of the city, Chicago 360 Observation Deck has added a feature that now allows visitors to tilt over the city of Chicago. Yes, we mean literally TILT! The Tilt experience is a small extra fee to the observation deck. You hold on to the metal handle bars and get prepared to tilt over the Windy City. Once you've experienced the once in a life time thrill ride head over to Bar 94 for amazing 360 views of the city and fresh cocktails. When purchasing your tickets, be sure to select the 40.00 All Access Pass. The All Access Pass gives you access to the 360 Observation Deck, The Tilt Experience, & includes one drink from Bar 94. You can book the All Access Pass, here. The 360 Chicago observation deck is a true city experience like no other.

Cupcakes in a ATM? Sprinkles 50 E Walton St. Chicago, IL 60611

After all that thrill seeking adventure you’re adrenaline should definitely be up and pumping. 360 Chicago observation deck was located in downtown Chicago and parking can be costly.

Pro Tip: Map out where a few of your ideal destinations are going to be and maximize as much as possible on parking.

The 360 Chicago Observation Deck was only a 6 minute walk to Sprinkles so we didn’t have to pay extra for parking. Once arriving to Sprinkles, you have the option to go inside and purchase a dessert, however sprinkles offers the cupcake ATM so why not use it. You have to have a debit/credit card, use the touch screen pad, and select the cupcake you want. Sprinkles is such a cute experience and the delicious cupcakes are definitely worth it.

New Home for the Week: Aurora, IL

As stated before we were interested in exploring Chicago and its surrounding cities. Therefore, we decided to continue to stay on the outskirts of town. We found an AirBNB in Aurora, IL which is still fairly close to Napierville. Right after Sprinkles, we headed back to Napierville to check into our Airbnb. The Airbnb is a two bedroom luxury apartment. We had access to the many apartment amenities such as the pool, gym, & clubhouse. This Napierville apartment was the perfect place for us to continue our Chicago stay.

Chicago Deep Dish:

Just like you can’t go to Nashville without trying Hot Chicken, you cannot go to Chicago without trying a Chicago deep dish pizza. We were advised that there is a competition between Lou Malnati’s and Giordano’s for the best deep dish Chicago style pizza. We initially planned on trying both places, however we were only able to accommodate one in our itinerary. Lou Malnati’s had the availability to seat us so we went with them. Since we were in the Napierville area, we decided to try the Downtown Lou Malnati’s Napierville location. This location has large open windows so we were able to experience some patio vibes. There is a full service bar and menu as well if you’d like a cocktail with your deep dish pizza. We ordered the Deep Dish The Lou & side Caesar salads. We enjoyed the Caesar salad more than we did the actual deep dish pizza. We didn’t have to have reservations for this locations and they were open until 11pm which helped accommodate our schedule and satisfied our late night craving. If you have the chance to rate Giordano’s against Louis Malnati’s, we’d definitely advise to try that. We noticed that everywhere in town if you saw one establishment you saw the other one close by, which shows how deep in competition both establishments are. We’d rate Lou Malnati’s a 7/10.

#SummertimeChiDay3: City Views

On Day 3 we spent most of the day in the city of Chicago. We started with a early start for breakfast at Batter & Berries. Batter & Berries are a black owned restaurant that caters to breakfast and brunch. The restaurant does not take reservations and is a first come first served establishment. Therefore, we recommend arriving when the restaurant first opens to avoid the brunch crowd and decrease having to wait long periods of time to be seated. The restaurant is known for its World Famous French Toast Flight. The French Toast Flight allows you to sample all of the French toast, which is strawberry, blueberry, lemon, and caramel. We also ordered a side of eggs and hash browns. The restaurant does not serve alcohol, however, they are BYOB and will provide you with any juice if you’d like to make mimosas for your brunch. We’d definitely recommend Batters and Berries and we’d rate this establishment a 9/10.

Lovers In The City:

After breakfast, we headed to Northbrook, IL which is where our next getaway was. We booked a four hour romantic getaway at Sybaris Pool Suites in Northbrook. Sybarius Pool Suites are known to be the getaway destination for couples. Sybaris offers a variety of pool suites to accommodate your romantic stay. We chose the Chalet Swimming Pool Suite. The Chalet Swimming Pool Suite is equipped with its own private garage, multi levels of luxury, private heated swimming pool with a tropical waterfall and water slide, hot tub, steam room, massage chairs, fireplace, and jetted whirlpool. The Chalet suite is a couples paradise. The price of an overnight stay runs anywhere between $529-649.00 USD per night depending on the day of the week you stay on. However, since we already had an AirBNB we decided to only do an afternoon getaway stay for the price of $219.00 USD plus tax. The afternoon stay allows you access to the Chalet for four hours which are between the hours of 12:30pm-4:30pm. Sybaris also has a variety of getaway packages that you can include in your suite as an add-on. For example, for an extra $30 we purchased a bottle of chain on ice, chocolate truffles and the souvenir champagne glasses. This entire stay was fun, romantic, and relaxing.

Downtown Views

After we checked out at Sybaris, we headed to dinner at the London House Chicago. The London House is a rooftop restaurant that is attached to the Hilton Hotel. The London House is known for it's beautiful rooftop and amazing views of the downtown area. Due to the popularity of the restaurant, you do have to reserve at least a month in advance to have a table. The link to reserve is here. There is a full bar and waitress to serve cocktails and a small food menu selection. We ordered the Vegan Burger and Parmesan Truffle fries. The food and drinks were okay, however the vibe and atmosphere was superb. We’d rate The London House Chicago an 8/10.

Pro Tip: For parking we paid a flat rate of $20.00 USD to the valet at the Hilton Hotel for the entire night. This allowed us to move around freely and we even got to venture next door to Ocean Prime which is right beside the London house. And we enjoyed more cocktails and desert at Ocean Prime.

Wake N' Bake

We started our day with breakfast at this new CBD Infused café called Wake N' Bacon. The café is located in the Lakeview Chicago area. We had an 8:00am reservation, which allowed us to easily find free street parking right across from the café. Due to the pandemic, the restaurant is currently operating at 50% capacity for the safety of its customers therefore you will need a reservation. You can make a reservation by clicking here. Wake N' Bacon is known for its trendy and Instagramable features. The café has a beautiful floral aesthetic. There is a huge mirror that’s actually a camera and you can take and print a Polaroid photo and post it on the photo wall at the café. For breakfast, we ordered the Spiced Maple Chicken n' Waffles & the Cocorazz Stuff French Toast. For drinks, we ordered the Purple Haze Coffee. The food was delicious. For an extra fee, you can add CBD to any of your food or drinks. Wake N' Bacon was definitely a whole vibe and we loved this café. We rate this establishment a 10/10.

Spending the Day at Navy Pier

After breakfast, we decided to spend the day at Navy pier.

Pro Tip: Parking at the Pier is extremely expensive therefore we recommend trying to arrive as early as possible, plan ahead & research all the activities you would like to do. The pier parking is definitely a tourist trap. Try to go to Navy pier during the weekday. It’s less crowded, the weekend is filled with tourist.

We arrived around 11:15 am and which was the perfect time because there was not a crowd for the Centennial Wheel. We purchased our tickets at the self service ticket booth and was able to enjoy aerial views of the city from the Centennial Wheel.

After the Centennial Wheel, we headed to Milton Lee Olive Park. The park is outside of the pier, however, it’s only a 6 minute walk from the pier. Milton Lee Olive Park has a nice balcony lake view of the city of Chicago and allows a great photo opportunity.

Once we explored the park, we headed back to the pier for drinks. We were still pretty full from breakfast and decided to have cocktails at Offshore. Offshore is located at Navy Pier and is noted to be the largest rooftop bar in the world according to the Guinness Book of World Records. We didn’t make a reservation, and did a walk in and was able to get a table on the outside roof top bar. We would suggest making a reservation, however. The view of the city, lake, and pier were amazing from Offshore and the cocktails & customer service was great. We’d rate this establishment a 9/10.

Murals and Things

After spending a few hours at the pier, we headed to the famous Greetings from Chicago mural. The mural is located at 2226 N Milwaukee Ave, Chicago, IL 60747. The mural is inside of a parking lot so it’s free parking while you get your shot.

Impromptu Travel is the Best

After the mural shoot, we were driving to eat dinner and stumbled across the Swan Boat Rentals. We saw some individuals out on a pond paddling in the swam boats and decided to pull in to see what the fun was all about. The park we pulled into was called Humboldt Park. The park contained surrey, choppers, and swan boat rentals. The swan boat rental was $11 an hour for an adult. The rentals came with free life jackets rentals. The swan boats were easy to paddle and was a very fun impromptu activity. If you are passing through Humboldt Park we definitely recommend this activity.

Can’t believe it’s not What?

After the swan boats, we headed to Can’t Believe It's Not Meat for dinner. Can’t Believe It’s Not Meat it’s a new black owned, hip, plant based restaurant. We went to the Orland Park location since this location was the newest one and provided free parking. For dinner, we had the Big Mic which is their version of the “Big Mac” and the Philly Cheese Steak Egg Roll. For drinks we ordered a Bad & Bougie smoothie & an Ice Ice Baby Shake. The food and beverages were delicious. The customer service and atmosphere was also superb. There is also an outside patio to the establishment as well which we loved. We definitely rate this establishment a 9.5/10.

#SummertimeChi Day 5: Parks, parks, & more parks.

Recently, we found this new profound love for hiking. While creating our itinerary for Chicago, we stumbled across this beautiful hidden gem called Matthiessen State Park. The park is located in Oglesby, IL which was about an hour in a half drive from Napierville and hour and 45 minutes from Chicago. Matthessian State Park is a fairly big size park. The park contains camp grounds, upper and lower dells, cascade waterfalls, sunflower field, multiple hiking trails, and picnic facilities. We started our day at Matthessian by going to the Sunflower field first. The sunflower field was packed with beautiful tall sunflowers. You are allowed to pick them and bring them with you as a souvenir.

Pro Tip: For the hiking trail you definitely want to have water shoes or hiking boots that you don’t mind getting wet. Also, remember to bring and use mosquito repellent.

After the sunflower field, we drove around to another park entry point and went to the hiking trails to start our hike. The hiking trails have plenty of signs that you can follow to decide which part of the trail you’d like to hike to first and explore to find the waterfall.

After the hike, we had reservations for another outside event which was the Morton Arboretum. The Morton Arboretum is an outdoor museum and a public garden. Currently, the Human Nature Walking Tour Exhibit by South African artist Daniel Popper is displayed at Morton Arboretum. The Human Nature Tour has five uniquely designed sculptures in various locations in the Arboretum. There is a East Side and West Side to the Arboretum. The sculptures are located throughout the different sides of the exhibit. The human nature exhibit does have a reserved date and time entry for guest on the website when you book. You can reserve your tickets here, the human nature exhibit will be displayed for a year.

#SummertimeChi Day 6: Cruises and things

You can’t do Chicago without heading out onto the beautiful Lake Michigan. We booked a lunch cruise on The Odyssey. The Odyssey is a 4 level luxury yacht. We booked the premier lunch cruise on Lake Michigan through Entertainment Cruises. The lunch included a salad, vegetables, & smothered chicken or fish. There was a bar on the yacht, however, alcohol was not included in the lunch & we had to pay an additional price for any alcoholic beverages. After lunch, we headed up to the observation deck to take in the beautiful view of the Windy City.

Pro Tip : The Odyssey cruise is located at Navy pier so utilize this time to do any activities at Navy pier or surrounding area to maximize your time on parking cost.

Chicago has beaches?

Yes! Chicago has beaches! Right after the Odyssey Cruise, we headed over to the Ohio Street Beach. The Ohio Street Beach is right next to Milton Lee Olive Park. There are beach front restaurants, volley ball, and definitely beautiful city views. There is also a lifeguard on duty for anyone that wants to swim. The Ohio Street Beach is the place to catch a beautiful sunset and enjoy some beautiful city beach vibes.

Greenhouse Vibes

Have you ever had cocktails in a greenhouse in a middle of a Chicago intersection? The Darling Chicago definitely gives you this opportunity. The Darling has a Rose Garden which consist of small greenhouses on an outside patio and small table and chairs inside of each greenhouse. The Rose Garden has a menu of small plates and creative cocktails. To book the Rose Garden, you have to make a reservation and pay a $10.00 USD per person deposit which is applied to the final tab. The Darling also has an inside section such as The Ballroom or The Library that you can reserve as well. The entire establishment was very upscale and chic. We rate the experience a 9/10.

#SummerTimeChi Day 7: Temples & Things

We always try to add in an educational or historical experience for our trips. The BAPS Shri Swaminarayan Mandir in Chicago was the perfect experience and was free. The temple is located on the outskirts of Chicago in Barlett, IL. The Mandir is a place of worship and prayer for followers of Hinduism, however the temple is open to the public daily from 9am-6pm throughout the year. There is a casual attire dress code. For women, if your dress or skirt is not knee length, then you will be requested to wear wraps which are provided in the temple. Once you’re inside of the temple, you must remove your shoes and place them on a shoe rack. The Mandir complex is a sacred and spiritual place of worship, therefore there is no photography on the inside of the temple, however you can take pictures outside of the temple. The architecture and structure of the temple is breathtaking.

Hey Sugar, Gimme Sugar

For lunch we tried this bakery called Hey Sugar. It’s a playful and fun café that’s located in downtown Geneva. The store has a beautiful pink flower and gold aesthetic. There are two cute Hammock chairs that you can sit and take a cute photo in. There is also a beautiful Instagramable bathtub and flower backdrop aesthetic for photos. For lunch, we had two of the most popular drinks on the menu. The Watermelon Dream Lemonade which comes with cotton candy and different candy pieces and the OG Lemonade which has a popsicle in it. We also had a Raspberry & Snickerdoodle cupcakes. There is an cute pink and blue outside patio if you’re wanting to enjoy some outside vibes. We definitely rate this café a 9/10.

Piece of Italy in Chicago

Ever heard of the Leaning Tower of Pisa in Pisa, Italy. Well, there’s a Leaning Tower in Niles, IL which is about 30 minutes outside of Chicago. The Leaning Tower of Niles is a replica of the Leaning Tower of Pisa. This national landmark is open to the public and has open parking. The tower does have a bell in it and at different times of the day you will hear the bell ring for several minutes. The Leaning Tower of Niles is half the size of Italy’s Leaning Tower of Pisa, however, it’s details and beauty still stand strong and is respected in the city of Chicago.

Goodbye to the Windy City:

Despite the negative remarks we heard prior to our trip, we enjoyed every bit of Chicago and plan to return soon. We felt very safe and enjoyed exploring different parts of the city, the food was great, the city was huge and beautiful, and it's safe to say that we survived Chicago! Summertime Chi was the perfect vibe.

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1 Comment

Aug 30, 2021

I️ can’t wait to travel with my husband like this!! Care feee and loved on! #ManningGoals ❤️

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