Plan a Girl’s Weekend Chicago Staycation in Rosemont

Plan a Girl’s Weekend Chicago Staycation in Rosemont

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Rosemont is Vegas.

There are no strip clubs (just strip malls) and there are no dance clubs.

You don’t go to Rosemont for the arts or the history. You go there to be entertained.

I took my first vacation for 2016 in Chicago. Part of being a city girl is having access to the international and national airport hubs, buses, and trains to go travel some place new. As much as I love Chicago, I also love that it gives me the chance to getaway.

I recently had the opportunity to experience Rosemont attractions and accommodations through a Rosemont Media Tour for a staycation. Though I have crashed with other people at Chicago hotels for conferences and other occasions, this was my first proper staycation.

The experience was quite perfect, and I want to share with you some highlights of the staycation for a Rosemont travel guide.

Transportation in Rosemont:

Getting to Rosemont is like traveling. You take the Blue Line north and west all the way to the Rosemont Blue Line CTA Stop. There were Pace buses (you can use your Ventra card) right at the Blue Line CTA Stop to drop me off right in front of my hotel, Loews Chicago O’Hare Hotel. My friend and I came right from work on Friday night for a girls’ weekend.

I had a moment to drop off my bags, and then a hotel shuttle took me right to MB Financial Park for a one-stop night of entertainment and of course, food and drinks.

Rosemont is walkable and offers free transportation to the main attractions. You don’t need a car because if the hotel shuttle isn’t taking you to your destination, there is a trolley, a bus, a train, or even your own feet can take you there. Everything really is that close.

You can be entertained longer in Rosemont. Most Chicago bars and clubs start closing down around 1:30 am. But in Rosemont, you will be entertained until 3:00 am—the time that most businesses close, including the candy store—when a complimentary trolley, the Entertainment Circular,  will take you back to your hotel.

There are many key sites in Rosemont for business and pleasure which include:

MB Financial Park for food and entertainment

The AllState Arena for music

Rosemont Theater for arts

The Donald E. Stephens Center for business conventions

The Fashion Outlets of Chicago for discounted shopping

Rosemont really is it’s own mini-city that is perfect for travelers from O’Hare International Airport to explore during a layover or for Chicagoans to have a weekend getaway because of the attractions and the transportation and nearby hotels and airport.

MB Financial Park: Non-Stop Entertainment

Rosemont is better than any block in Chicago for entertainment because the majority of the entertainment and restaurants is in one giant circle, MB Financial Park (5501 Park Place).  Within this 200,000 square feet circle, you have your choice of international cuisine, movies, live music, and comedy.

Don’t get me wrong, Chicago has some great neighborhoods to explore and world-class entertainment and accommodations, but sometimes you want a convenient bar crawl.

During the winter, the center turns into an ice skating rink for the first part of winter and then solely a hockey rink for the rest of winter. On the side is a mini snow slope for sledding.

Rosemont Restaurants:

What I love most about MB Financial Park is that there really is a different flavor and flare at each restaurant. While I was in Rosemont for a staycation, I was able to sample multiple restaurants. As a Floridian, I felt like I was visiting different countries like at Universal Studios because each restaurant expressed a different culture and at the very least, created an entirely different atmosphere—while at the same time being fun and exciting.

There were your calmer, more relaxing spots like the Muvico Theater and Park Tavern, but having a pub crawl is just too easy, especially with the trolley service at the end of the night.

Adobe Gila’s Margarita Fajita Cantina guarantees homemade guacamole and fresh margaritas. The entire restaurant is transformed into positive vibes and tropical theme despite Chicago winter’s stark contrast.


Fogo de Chao Rosemont dining room
Fogo de Chao Rosemont dining room. Photo Credit: Fogo de Chao


The best food in Rosemont was at Fago de Chao. Oh, my word, the jumbo shrimp was so fresh, and the meat was cooked to perfection. Fago de Chao offered Brazil’s national drink—yes, Brazil has a national drink—the Caipirinha, but their food was far superior. They offer a full salad bar, generous meat portions, and a classy, upscale environment for business meetings or a nice dinner out for a romantic staycation.

Live Entertainment with Dinner:

I really felt like I entered a different country when we ate at Hofbrauhaus Chicago, a German restaurant complete with live German singers and musicians, and authentic German beer served with soft pretzels alongside the standard cheese dips and mustards.

There was also live entertainment at Five Roses. Five Roses reminded me of Lady Gregory’s in Andersonville because we sat in the back in the library. We tried English fish and chips and paired it with Old Rasputin’s, a heavier drink. On a Friday night, they had a live singer and guitarist. He had a John Mayer vibe.


The library room at Five Roses Irish Pub in Rosemont.
The library room at Five Roses Irish Pub in Rosemont. Photo Credit: Five Roses


Candy and Drinks:

For drinks, I would actually go to the candy store. Don’t skip The Sugar Factory. They have a bouncer outside because  you are sure to leave with a sugar high or, at least, a bucket of candy. The Sugar Factory has too many types of sweets to offer from the sweet and sour to the chocolate dipped nuts and pretzels. We decided to grab our bucket of candy after laughing the night away at Zanies. Don’t miss the opportunity to take a photo behind The Sugar Factory banner.

Park Tavern is just that, a tavern. Their food is above average bar food, and their drinks can get super sweet. However, the favorite beverage of the night went to the Park Tavern for their cherry drink—The Irish Soda—with Cruzan black cherry rum, Jameson Irish whiskey, and Sprite.

Kings Bowl
Kings Bowl in Rosemont. Photo: Amanda Elliott

Another favorite drink was at King’s Bowling Alley. They have a fruity drink, Sour Patch Kings, with Sour Patch Kids candy inside. It’s an actual fish bowl and also has Tequila, Midori, Fresh Lime Juice, Orange & Apple Liqueurs, Blue Curacao, Sour Mix and Sour Patch Kids Candy with a Sugar Dipped Lemon. Bring friends to help you as you drink and bowl at King’s Bowling Alley.

For beer lovers, you can’t pass up, Hofbrauhaus, though. Their beer is really good. We tried the Dunkelgold, a malt flavored beer.


A Night in Rosemont:

We were offered to eat the world, but we decided to drink it instead.

One of the most anticipated activities of the night was indoor skydiving at iFly.


Indoor skydiving at iFly in Rosemont.
Indoor skydiving at iFly in Rosemont. Photo Credit: iFly

Be warned, iFly is a sober activity. I suggest starting with skydiving. And after that high, drinking your way into the night and ending with comedy at Zanies.

It can also be overwhelming to do everything Rosemont has to offer in one night. I think you need a good drinking and entertainment night in Rosemont and then a fun, active day of shopping and indoor skydiving.

After eating and drinking in Rosemont, we had the option to do indoor skydiving, bowl at King’s or laugh at Zanies standup comedy club.

Zanies Comedy Club:

We opted to laugh in Rosemont. Chicago has some great comedians, and I have been to Second City, Up Comedy Club, iO Theatre, and The Laugh Factory, but honestly, I haven’t laughed as hard as I did at Zanies.

Zanies Comedy Club in Rosemont. Photo Credit: Amanda Elliott
Zanies Comedy Club in Rosemont. Photo Credit: Amanda Elliott

Zanies is strategically set up on one-level so that everyone can see the comedian, Cyndi Nelson, the General Manager told us over Mango drinks. I greatly appreciated this because we were late to the 8:00 pm comedy show. Even though we were seated in a booth in the very back, I could still see the comedian the whole time. In standup, body language is just as important as the punchline.

The first comedian was funny. His best joke was about his height.

The headliner was James Davis, a writer, comedian, and reoccurring guest performer at the B.E.T. awards. Davis was amazing. Everyone agreed. He brought us back to Boy Scouts, to the days of high school, and then added in lines about being a closer on Christian Mingle dating to being that one black friend.

Davis called himself a California roll.

“If black people are sushi, I’m the California roll. Go to some other hood for wasabi.”

The best quote of the night was:

“Being in yout 30s is like being in the same party bus in your 20s, but being in it on your way home.”

Like most comedy clubs, there is a two drink minimum at Zanies. There is also a special dinner at a local restaurant and Zanies comedy club combo.

Staycation Accommodations:

After a really good night, we started phase two of girl’s weekend back at our hotel, Loews Chicago O’Hare Hotel, where we received fruit and Fiji and slipped into our comfy robes. All I need in life is a comfy robe, fruit, and Fiji.


My friend and I had a private tour of the hotel and saw the art gallery in the hotel with pieces priced at $70,000.00. We also toured the banquet halls, where we stood beneath gigantic rose-shaped light fixtures.

Art gallery at Loews Hotel in Rosemont.
The art gallery at Loews Hotel in Rosemont. Photo Credit: Amanda Elliott

We then met the Sous Chef, Scott Becker, at The Ashburn, the restaurant at the hotel which took its name from Chicago’s first airport.  Becker took us on a tour through the kitchen, where they were slicing what appeared to be dozens of apples for their homemade Whiskey Apple Cobbler. This new restaurant opened two months ago and includes unique features like sectioned off barn doors.

That night, we had a nightcap. The Ashburn has 13 beers on tap, though not Stella. We decided on cocktails and chatted with other guests on the media tour over popcorn, which I promise tasted like pickles.

Becker explained that he adds different garnishes to the popcorn.

We had a good stay at Loews Chicago O’Hare Hotel, but it is definitely set up for business clientele due to their conference space, huge lobby, and proximity to the airport. It was a great stay for a staycation, it was only missing a pool.

Our hotel room faced west,  but if you get a hotel room that faces east, you can wake up to a picturesque skyline view of Chicago.

Loews Rosemont hotel lobby.
Loews Rosemont hotel lobby. Photo Credit: Amanda Elliott

The next day we had brunch at The Ashburn. The smoothies on ice, the fresh orange juice and the fruit and yogurt parfaits were a perfect way to jumpstart a day of shopping.

The Fashion Outlets of Chicago:

A girl’s weekend staycation trip would not be complete without shopping. The Fashion Outlet of Chicago is huge and it is right next to Loews Chicago O’Hare Hotel.

The hotel shuttle dropped us off right in front. We met at the concierge service, where they took our coats and our bags, for a hassle-free shopping experience.

A guide pointed out new additions to the 130 shops including LuLu Lemon, which just opened this winter and now ships all of their sale items to this fashion outlet location.

We also learned about British fashion, with shops like L.K. Bennett, where Kate Middleton finds her infamously stylish shoes.

The Art of Shaving shop in Rosement
The Art of Shaving in Rosemont. Photo Credit: Amanda Elliott

My favorite shop was actually The Art of Shaving. Yes, it’s for men, but I was part of the demonstration and learned how to exfoliate, brush, and have a proper shave for men and women. My hand never felt so soft—and I have very soft skin. The cream that we apply protects our skin, but the key step that women miss is exfoliation, which you achieve through rubbing in the cream with a brush. The silvertip brush, which lasts almost a lifetime retails for $195 at the outlet location.

Michael Kors in Rosemont. Photo Credit: Fashion Outlets in Chicago
Michael Kors in Rosemont. Photo Credit: Fashion Outlets in Chicago

My friend and I went home with something from The Limited. I kind of love The Limited, Ann Taylor, and the Banana Republic. The Limited had better selection and pricing than the Banana Republic at this mall, though.

Overall Recommendation:

I am all for a weekend getaway with arts and entertainments and exploration, like my 48 hours in Charlotte, NC experience. But sometimes, it’s nice to stop planning and start relaxing and enjoying. That is what a Rosemont staycation can do for you—provide an entertaining vacation in one-stop without the lines and with all the perks.

A travel guide took us to almost all of the restaurants in the MB Financial park. She was amazing and informative. Alex Jakubiak from Carol Fox and Associates helped with the planning and logistics of the media tour and she was organized, responsive, and a key player in making my stay at Rosemont so enjoyable.

When you’re planning your Rosemont staycation, I would recommend at least one night in Rosemont. This will give you enough time to fully enjoy the nightlife and restaurants in the MB Financial Park at night, take advantage of the great hotels, and wake-up to indoor sky-diving and perhaps shopping the next day.

Where’s your favorite place to have a staycation in Chicago?



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