A few weeks ago I had the foodie weekend of a lifetime! Together with my bestie Alli of Cupcake Diaries we ate our way through the city of Chicago in the best possible way. In just a weekend we managed to see and eat more than we could have imagined and had an amazing time in the process. We flew out of Salt Lake City on a Friday night and spent until Monday afternoon in the Windy City. I’ve rounded up our collection of what we feel is the best of the best. If you’re planning a trip soon or have a trip booked already, this is your ultimate guide to making the most of your time!
One of the breakfast hot spots is Wildberry Pancakes and Cafe. When I say hot spot, I really mean it. The wait was an hour and 30 minutes… and worth every minute of waiting. Thankfully the famous Bean is right across the street so we were able to kill time by checking off one of our ‘to do’ items. Worked out perfectly! I got a Wildberry Orange Juice (which was absolutely divine, but on the sweet side – so beware if you’re ordering a sweet breakfast it may be a little much). For my meal I ended up with the “Signature Berry Bliss” French Toast which was TO DIE FOR! It was a hard decision as I wanted to order #allthethings but I’m really happy I went with the french toast. I’m not going to lie, I finished every last bite. Evidently the ‘Signature Berry Bliss” is well… their signature! Ha! You can get that style of pancakes, Belgian Waffles, crepes or the french toast. I tasted Alli’s pancakes and they too were divine, so I’m guessing that if you choose any of the above you’ll be very happy with your choice!
The iconic ‘Bean’ is a must see attraction. It’s actually called “Cloud Gate” which was news to me when I googled it. It is free to walk around and take as many pictures as you like. There’s something fun about snapping your photo in the reflection.
“The Bean” | 201 E Randolph St Chicago, IL 60601
Always Open | Fun All Year Round
You may be familiar with Magnolia Bakery from New York City but there’s a location in Chicago as well. We made certain to add this to the list of must visit places. I had actually been to the bakery when I went to NYC in 2014 but didn’t know of how amazing the ‘famous banana pudding’ was. That was at the top of my list to try this trip. It was indeed everything that everyone has talked it up to be. If you have the chance you must go and you MUST get the banana pudding. It’s layers of vanilla wafers, fresh bananas and creamy vanilla pudding and a small will only cost you $3.75 (which was the perfect portion size).
One of the best tips we were given was to purchase a Chicago City Pass. It’s another one of those things that I had done in NYC so I was happy to hear that Chicago had one as well. You get the option to visit five large city attractions for one flat price at a savings of over 50%! We purchased one and were able to make it to four out of the five attractions. The first was the Skydeck. You travel to the 103 floor of Willis Tower (formerly known as Sears Tower) which is the tallest building in the western hemisphere. Not only do you get to see the most majestic views of the city, you also have the option to do out onto ‘The Ledge’ which extends 4.3 feet from the Skydeck. As brave as Alli and I initially thought we were, in the end we were too chicken to do it. I’m severely afraid of heights and it just wasn’t going to happen. We gave it a valiant effort though and still enjoyed the views… from within the Skydeck!
Skydeck Chicago | 233 South Wacker Drive Chicago, IL 60606
Winter (Oct-Mar): Open daily, 10am-8pm Last admission 30 min. before closing
One of the attractions available on the city pass is for The Art Institute of Chicago. Believe me when I tell you that this place is MASSIVE. You pretty much are going to want to carve out at least half a day if not a whole day to get to see everything. There’s so much to be seen, but if you’re running short on time they’ve got a cool ‘fast track’ plan on their museum guide that will walk to through the most popular pieces in about an hour. We took that route and still only made it about halfway through.
The Art Institute of Chicago | 111 South Michigan Avenue Chicago, IL 60603
Mon-Wed & Fri-Sun, 10:30am-5pm
Something you may not know about me is that I LOVE the Chicago show series Chicago Fire & Chicago PD. I’ve been watching them religiously on t.v. for the past several years. I haven’t gotten on board with Chicago Med only because I don’t care for medical shows. I will be watching the newest spinoff Chicago Justice though! I had researched before our trip and learned that the station that Chicago Fire is filmed at was only a few miles from our hotel. We ended up missing the lunch spot we were going to eat (because they closed at 2:00 pm and we weren’t paying close enough attention to the time) so it gave us an extra hour after the art institute. We gabbed a Lyft and made our way over.
I was as giddy as a school girl to see the station and of course took plenty of pictures of the outside. I walked around the side of the building, the front, across the street and then to the back. I noticed as I was snapping pictures of the back that there was a firefighter (an actually firefighter, not an actor) enjoying the warm weather outside. I mustered up the courage and walked over to introduce myself We struck up a quick conversation and then he invited us on a tour of the station. Due to the popularity of the show they no longer film inside of the station but he gave us a tour anyway. It was a surreal experience and SO MUCH FUN! We were there for probably an hour hearing about the station, firefighters, the gear and equipment and even the differences between a truck and an engine. It was all so interesting!
Engine 18 Chicago Fire | 1360 S Blue Island Ave Chicago, IL 60608
Please do me a favor and add Maggiano’s to your list of places to eat. You have to, have to, have to. It was one of the most incredible dining experiences that I’ve ever had. For a foodie, that’s saying something. Alli and I were originally going to dine at Frontera down the street but the wait was too long so we walked to Maggiano’s instead. It was destiny. We were seated almost immediately in the bar area. Everything from the service to the food was impeccable.
We started with the Calamari Fritte with Marinara Sauce which was absolutely delicious. For my entree I ordered the Famous Rigatoni ‘D’ which is “Herb-Roasted Chicken, Mushrooms, Caramelized Onions, Marsala Cream Sauce”. I kid you not when I tell you that it was the best rigatoni that I’ve ever eaten. For dessert we finished up with the Mini Dessert Sampler. Oh. My. HEAVENS TO BETSY!!! First of all I didn’t have enough room for dessert. Second of all I made room for dessert anyway. It came with Tiramisu, Gigi’s Butter Cake, Apple Crostada and New York Style Cheesecake. The butter cake tasted like a freaking delicious doughnut. Holy. Cow. It was definitely my favorite of the four. It had a crispy yet not-too-crispy outer crust and a soft fluffy inside. The Apple Crostada was to me ‘the ultimate apple pie meets apple crisp’. Crispy crust with large sugar crystals. It was SO divine. Definitely my second favorite of the four. I’m telling you. This meal changed my life in the best possible way. Todd Houchin the Managing Partner rolled out the red carpet for us and gave us an incredible experience. Thank you Todd, it was unforgettable!
Another breakfast hot spot is Toni Patisserie & Cafe. If you take a look at their menu online you’ll surely fall in love with one thing or another. Because I couldn’t decide… and because I wanted to try both… I ended up ordering the Toni Benedict which is “Poached Eggs, House Made Buttermilk Biscuit, Parisian Style Ham, Hollandaise Sauce, Breakfast Potatoes” along with a Crepe Suzette which is “Cognac, Orange Liqueur, Orange Juice and Zest and Orange Supreme, with Carmelized Sugar and Butter”. Both were delicious, although the biscuit on my Benedict seemed slightly overcooked. That didn’t of course stop me from eating the entire thing! Additionally they have an assortment of French Macarons so I of course had to get a box of those.
Toni Patisserie & Cafe | Menu | 65 E Washington St, Chicago, Illinois 60602
Breakfast & Brunch | Monday-Friday 7 AM to 7 PM, Saturday 8 AM to 7 PM, Sunday 9 AM to 5PM
Another attraction included in our city pass was the Shedd Aquarium. It’s been years since I’ve been to an aquarium so I was really excited to visit this particular attraction. It was HUGE! So much to see and do. One of the perks of the city pass is that you get to bypass the line (if there is one) and go straight to the front (similar to a fast pass). On the day we went it was some sort of passholders appreciation day or something and the line was wrapped around the park. It was the best perk getting to avoid waiting hours to get in. We were able to see so much in the couple of hours we had free, it was a great way to spend the afternoon!
Shedd Aquarium | 1200 South Lake Shore Drive Chicago, IL 60605
Winter: Mon-Fri, 9am-5pm; Sat-Sun & Holidays, 9am-6pm
There’s a battle of the best pizzas and we happened to try both. When I asked friends for recommendations on where to eat it was almost split down the middle of those voting for Lou Malnati’s or Giordano’s. Because I had been to Giordano’s on my 2015 visit to Chicago I was eager to give Lou’s a try to see which I would personally find better tasting. From what we heard you HAD to try the butter crust as it was not to be missed. So after the aquarium Alli and I headed to Lou Malnati’s for lunch. From the start it was a rough experience. Somehow I put in the wrong location for our Lyft driver to drop us off at so we ended up going 2 1/2+ miles out of our way. Then had the rockiest experience throughout our entire meal. We really wanted to be able to show you a legendary Chicago pizza ‘cheese pull’ but it just wasn’t in the cards.
We started with the Garlic Bread with Marinara Sauce (if you ask Alli, looked like a trout.. hahaha!) and then shared a deep dish pizza with sausage, pepperoni, olives and mushrooms on half. The pizza wasn’t horrible, but it certainly wasn’t the best in the city either. Our server seemed to be in a hurry the entire time we ere eating and in fact left about 3/4 the way through our meal upon which we got a new server. For dessert we had ordered the Chocolate Chip Pizza (supposedly a signature item) which was a “freshly baked chocolate chip cookie prepared in a deep dish pizza pan, topped with vanilla bean ice cream and whipped cream.” It was an absolute disaster. The menu says to order after your first slice of pizza because it takes 10 minutes to bake, which we did. By the time we got it about 25-30 minutes had passed and not only was it cold (the bottom of the pan was absolutely cold to the touch) you couldn’t even see the cookie for the layer of entirely melted ice cream and a mess of whipped cream (to cover up the melted ice cream). We’re foodies. We’re not idiots. We could tell the cookie had probably been forgotten about, so we kindly requested a new one. The second time was a charm but because the whole experience had been tainted we hardly enjoyed it. In case you want to try it for yourself or avoid it, I’ve added it to this guide for you!
Because lunch had gone so long at Lou Malnati’s we missed going to The Field Museum as we had originally planned. The last admission was at 4:00 pm and we were wrapping up lunch around 3:50 so we knew we woulnd’t make it. Instead we walked to Navy Pier. We hadn’t added this into our plans but it was nice that we ended up having time to check it out. “Navy Pier is a 3,300-foot-long pier on the Chicago shoreline of Lake Michigan. It is located in the Streeterville neighborhood of the Near North Side community area.” It was a really beautiful view of the lake but not much to see or do aside from that. There was the ferris wheel but we opted not to do that. Mostly everything else was restaurants but we had just eaten. So we walked up and down the pier and then headed back towards our hotel.
Navy Pier | 600 E Grand Ave, Chicago, IL 60611
Monday – Thursday 10AM–8PM Friday & Saturday 10AM–10PM Sunday10AM–7PM
On our way back from Navy Pier we stopped at a bakery that was recommended to us. We weren’t originally going to be able to fit it in but we happened to be walking right past it on our way to dinner so we stopped in. It was a pretty adorable bakery and had a fair amount of cupcake selection left at the end of the day surprisingly. I got ‘The Ron Bennington’ which is chocolate cake, peanut butter filling, chocolate ganache, and crushed butterscotch topping. It was insanely rich, but also insanely soft, insanely chocolatey and the perfect amount of peanut-buttery. If you happen to be in the neighborhood this is definitely worth a stop. You can even ‘create your own’ cupcake creation if that tickles your fancy!
If you love steak you have to add the Chicago Cut Steakhouse to your plans (reservations recommended and easy to obtain online). I’m not generally a steak kind of girl but we had heard such phenomenal things we knew we just had to try it. Because we were at a steak house I of course ordered a steak. I ended up going with the USDA Prime Filet Mignon Center Barrel Cut (6 oz) and Alli and I shared the Truffle Scalloped Potatoes. The steak was absolutely divine but the nail in the coffin for me were the potatoes. They were quite possibly the best scalloped potatoes I’ve ever had in my LIFE. For real. We had to practically be rolled out of the restaurant. We were absolutely beyond stuffed. Beyond.
One of my hands down absolute favorite desserts is doughnuts. Love. Love. LOVE them with my whole heart and soul. There were two doughnut shops that we had the choice between, and while we didn’t get to the second one I feel that we made the right choice with Do-Rite Donuts. Had we not been going to lunch two hours after breakfast I would have tried the chicken sandwich also but we didn’t have enough time to let that digest so we stuck with the doughnuts (priorities right?). We ordered a half dozen and shared bits and pieces of each. We chose to try the Cinnamon Old Fashioned, Blueberry Crumbcake, Vanilla Bean Glazed, Candied Maple Bacon, Double Chocolate Old Fashioned, and Valrhona Chocolate Cake. Here’s what I thought of each:
- Cinnamon Old Fashioned
- Yum. Yum. Yummy! This one was really good. The perfect amount of crispy outside with a soft inside and wonderfully cinnamon-ee
- Blueberry Crumbcake
- Excellent – definitely recommend! There are little pockets of blueberry filling disbursed throughout that are a pleasant surprise.
- Vanilla Bean Glazed
- As boring as plain glaze is, this was in my top three favorite. The simplicity was nice.
- Candied Maple Bacon
- Good for a maple bacon. Maple Bacon doughnuts are just OK to me in general and this one wasn’t any more special than any others I’ve tried. It was good but I probably wouldn’t order it again.
- Double Chocolate Old Fashioned
- I liked this but be forewarned it is very rich. Delicious, just very chocolatey
- Valrhona Chocolate Cake
- Personally the chocolate frosting was a little too much on this one. It was probably my least favorite
The last attraction we went to was 360 Chicago. As if The Skydeck wasn’t enough of a heart attack inducer we decided to head to the top of the John Hancock Building to see ‘Tilt’ which is Chicago’s newest thrill. Remember the ledge I was telling you about at the Skydeck? Imagine if you will, tilting outward on a 30 degree angle at over 1000 feet above the Magnificent Mile. Yea that was a hard no from both of us. But we did take in the breathtaking views once more. If you’re into thrills this would be right up your alley.
360 Chicago | 875 North Michigan Avenue Chicago, IL 60611
Open daily, 9am-11pm Last entry is 30 minutes before close
The battle of the pizza I was telling you about? Giordano’s is the clear winner in my book. Hands down. We went for lunch and got the lunch special which was an Individual 6″ Pepperoni Stuffed Deep Dish Pizza with a side Caesar Salad. The pizza was so good I kid you not I almost wanted to order a second one (oink oink). What’s better about it than Lou Malnati’s? Better crust. Better sauce. Better cheese. Better everything. Just so much better.
Lastly, we stayed at the Whitehall Hotel which is a quaint boutique hotel in a really great location. If I had to guess I’d say we walked about 75% of the time and got Lyft rides the other 25%. In fact, Alli was wearing her FitBit and here’s the breakdown of our steps over our weekend: Saturday we walked 11,793 steps, Sunday we walked 26,197 steps and Monday we walked 15,943 steps. The great thing about Chicago is that it’s a really walkable city. I love walkable cities (like New York and Portland). Be careful not to end up in the sketchy part of town at night… that may have happened to us on the way to dinner on Saturday night. We felt perfectly safe until all of the sudden we took a turn down a street and didn’t feel safe at all. So steer clear of that (our husbands wouldn’t have been too pleased).
The Whitehall Hotel | 105 E Delaware Pl, Chicago, IL 60611
A couple of places that we hit up but didn’t photograph (too big of a hurry) were Garrett’s Popcorn: a MUST if you go to the city and you must get the Chicago Mix. We also hit up Eataly Chicago which was quite charming and totally worth checking out at least once.
Garrett’s Popcorn | 625 North Michigan Avenue Chicago, IL 60611 (although there are a locations everywhere)
Popcorn | Mon – Thurs 10:00 am – 8:00 pm, Fri – Sat 10:00 am – 10:00 pm, Sun 10:00 am – 7:00 pm
Eataly Chicago | 43 E Ohio St, Chicago, Illinois 60611
Specialty Grocery Store | Market: Monday-Saturday, 10 a.m.-11 p.m.; Sunday, 10 a.m.-10 p.m.
So there you have it. A good mix of things to eat and see in the great city of Chicago. If you happen to go I’d love to hear about it. If you need more ideas while planning I’d love to help. I created a killer spreadsheet that made for a pretty seamless trip and I’d be happy to share it with you if you would like it. Just shoot me an email and I’ll get it right over to you!