Looking for a fun way to spend a weekend in Chicago? I’ve got the perfect Chicago weekend itinerary here.
My best friend Amanda and I take a yearly “bestie” trip. We’ve done road trips to places both near and far and the last few years we’ve gotten into walkable cities (i.e. cities you can visit without needing a rental car). Last year we saw everything Boston had to offer and this year we explored Chicago.
Since we only had a 3 day weekend, we crammed everything we could think of into our trip. So if you’re looking to explore Chicago and you’re only working with a few days, this is going to be the perfect guide for you!
Day 1
Hyatt Regency
This is one amazing hotel. Its location is perfectly situated a couple blocks from the Navy Pier, Magnificent Mile, and Millennium Park (where “the bean” is). It’s got tons of amenities too! There are restaurants, a larger than most gym, and plenty of places to sit and work, talk, or people watch with a gorgeous view of the skyline.
The Dearborn
Not far from our hotel, we found this delicious restaurant. We had a reservation for lunch, and it’s a good thing we had it too because it was really busy when we arrived. We got a great table near the open windows and it was a perfect, breezy day for dining al fresco. The décor here is absolutely stunning. It feels so high end and would be a great spot for a business lunch or date night. My friend and I both ordered the Dearborn Burger, and I got mine with added bacon and caramelized onions. It was delicious! We loved this place and would eagerly go back!
Millennium Park
Seeing the Millennium Cloud (aka “the bean”) is one of those must-see things while in Chicago. It takes all of 5 minutes to see it and it’s a great place to get that signature picture for Chicago.
Buckingham Fountain
If this fountain looks familiar, that’s because it’s been featured in a lot of things like the tv show Married With Children, Crime Story, Amazing Race, Shameless, The Great Food Truck Race, and movie National Lampoon’s Vacation. This Grant Park fountain was dedicated in 1927 and is one of the largest fountains in the world.
Maggie Daley Park
If you’re looking to relax a bit, walk around Maggie Daley Park. There’s gorgeous lush green spaces to sit and relax, as well as a bunch of fun things to do for the kids like rollerblading at the ribbon, climbing the rock wall, play on the playground, mini golf, and grab some Ice cream.
Lakefront Trail
If you’re looking for great views of the city and Lake Michigan, then this is the place to be. This 18.5 mile paved path is used for walking, running, skateboarding, and cycling along the western shore of Lake Michigan. It’s nice a nice area to take stroll, enjoy a picnic, or just watch the boats go by.
Giordano’s
When we asked most people for their recommendations on the best deep dish pizza in Chicago, 9 out of 10 of them recommended this place – Giordano’s. First of all, expect a wait for your table, Also, it takes 45 minutes for a deep dish to be made and 30 minutes for a regular, so be prepared to hang out a bit before your food actually arrives. If you’re in a hurry, I recommend making an order ahead of time and just going to pick it up. We had the personal deep dish pizza (6” diameter) and the chopped salad. Both were out of this world delicious.
Day 2
Wildberry Cafe
If you’re a fan of breakfast food, then you need to get up a little earlier, roll out of bed, and head to Wildberry Café. This place was referred to us by a couple people, so we decided to try it out. We didn’t have a reservation, but we got to the restaurant around 8am and only had to wait for a few minutes. But let me tell you, that place got full, fast. So if you’re planning on trying it out, go as early as possible. They have all the classics here like omelettes, biscuits and gravy, and eggs any way you want it. But they also have some amazing looking pancakes and French toast that they’re most known for. This is the kind of place you can go back several times and find all sorts of things on the menu that will make your mouth water.
Navy Pier
The views from the Navy Pier are just stunning. We walked from our hotel out onto the pier and I have to tell you, it’s a lot bigger than I thought it was going to be. The pier is a 3,300 foot long pier on the shoreline of Lake Michigan in the Streeterville neighborhood of Chicago. Built in 1916, this area has seen a ton of growth over the last century and is a great place to spend a few hours or whole day. There’s rides and attractions, cafes, shops, cruise tours, and even a children’s museum. You can even spot a lighthouse not too far off shore.
Architecture River Cruise
If you love history, architecture, or just sightseeing in general, you’re going to want to take this river boat cruise tour. We boarded the boat for the mid afternoon cruise and got a seat near the back. The boat was probably about half full, so we didn’t feel cramped or too close to others. There’s a full bar on the boat, as well as restrooms if you need it. Our tour guide Becky was the best! Her sarcastic humor was right on point with us and we enjoyed every minute of this tour.
We learned that the skyscraper was actually founded in Chicago. And had the great fire of Chicago never happened, the city would look vastly different than it does currently. There were lots of interesting facts, historical points, and things to see. I would say this is a ”must” when visiting Chicago.
Magnificent Mile
If you’re a shop-a-holic, then this is the street for you. Luxury stores, big brand names, and little boutiques is the name of the game for the Magnificent Mile. You’d also really like walking along this road if you’re window shopper, because there’s a lot to see!
360 Chicago
Up on the 94th floor of the Hancock building, you’ll find the absolute best views of the city. It overlooks the Lakefront Trail, Harbor, and Lake Michigan on one side and then the city’s skyscrapers on the other. This was well worth the money to go 1000 feet above the street level. There’s also something at the observation deck called TILT. This is a unique way of seeing just how high up you are by standing on a platform that gradually tilts forward until you’re staring all the way down the side of the building. The people doing it seemed to be having fun, but the long line to do it wasn’t worth it for me.
Plus, that view from the top really couldn’t be beat. It’s gorgeous! You will want to check the weather before you go though – if it’s cloudy, you most likely won’t be able to see anything below you. One last tip – if you don’t feel like going where the crowds are (or you’re looking for a cheaper option), head to the 95th floor instead. There, you’ll find The Signature Lounge – a cocktail bar that has the best views of the city – just make sure you bring money to cover the two drink minimum.
Portillo’s
Every single person we told we were going to Chicago told us we just had to eat at Portillo’s. So when a restaurant comes with that high of praise, we listened. We got there around 2pm or so and the line was almost out the door. This place is always busy, so going at off peak times really isn’t a thing. Once we got inside, we figured out that it would be faster to order online and pickup at the counter. So that’s what we did. We went and got a table, ordered our food online and it was ready within 10 minutes.
I highly recommend this tactic because that counter service line was not moving very quickly. Portillo’s is known for their Chicago hot dogs and their Italian beef w/ sweet peppers sandwich. I didn’t try the hot dog, but that Italian Beef sandwich was out of this world delicious. And whatever is in that sauce they put on it is heavenly. I’d easily go back here again (and try the chocolate cake shake next time).
Wrigley Field
Since my bestie Amanda is a huge baseball fan, of course we had to see the iconic stadium since we were here. It’s not really close to anything else touristy, so you’ll need to take a short Uber ride over to it and back. Normally, you can take stadium tours, however Lady Gaga was putting on a concert the day that we were here, so they didn’t have any tours running that day. But it was still really great to see the real deal and walk around it.
Remington’s
There’s a lot of great restaurants over by “the bean”. One in particular is Remington’s. We made a reservation beforehand (which we figured out is a must anywhere in Chicago). Together, we had the lobster deviled eggs, crab cake, and steak salad. Everything was delicious! Our waiter was very friendly and attentive and we got to sit in a table next to the open windows and listen as the street performers played down the street a bit.
Day 3
Big Bus Tour
I’ve only done one other bus tour in my life and that was almost 20 years ago in NYC. But if I can recommend anything to do in Chicago, it’s this. Basically, with the bus tour you’re driven around to landmarks in the city and have certain stops the bus makes along the way. While you ride, you listen via headphones to the history of the places around you and it makes for a really great drive! Once you arrive at a bus stop, you can either choose to jump off and look around there or stay on and ride to the next destination. Buses will come every 30 minutes to the stops, so whenever you’re done exploring that area, you can just jump on the next one that shows up. We got to see places like:
- Willis tower
- Chicago Picasso
- Solider Field – Chicago bears’ stadium
- Adler planetarium
- Shed aquarium
- Field museum
Pro tip: use the bus tour as transportation to get anywhere you need to in the city.
Union Station
Before we went on the Big Bus Tour, we knew we had a couple stops we wanted to get off the bus at. The first was Union Station near Willis Tower. This beautiful Amtrak station is home to a major train hub. You can board a train to locations both near and far and the Great Hall inside is just stunning! It was built in 1925 and altogether the train station takes up about 10 city blocks. The Great Hall has a 219 foot long barrel-vaulted skylight that soars 115 feet above the floor. While it is a working train station, its beauty has captured the attention of those in Hollywood, as Union Station has been used in movies like My Best Friend’s Wedding and The Untouchables.
Doc B’s
Another Big Bus Tour stop brought us to a restaurant near the Magnificent Mile – Doc B’s. We didn’t have a reservation, but we were able to be seated at one of their last open tables for lunch. We had the guacamole with sweet potato chips, chicken sandwich, and the knife and fork cobb salad. Everything was absolutely delicious. Our waitress was super friendly and we were able to get in and out pretty quickly so that out tourist adventures could commence.
White Sox Game (at Guaranteed Rate Field)
When your home team (the Astros) are in town, you go see them wipe the floor with the White Sox at Guaranteed Rate Field. The stadium itself is great! It’s got plenty of seating and lots of different food options (even a couple restaurants for those that are gluten intolerant).
The Gage
Over by the bean yet again for dinner. This time, we’re at The Gage. We made reservations and were seated right away once we arrived at the restaurant. We were able to sit outside on the patio and it was so nice to relax with the breeze gently blowing. This restaurant had some really delicious food! We ordered the colossal prawn cocktail, 10 oz Filet, and the buffalo cauliflower. The shrimp cocktail was delicious and had 4 massive prawns on it. The filet was delicious and I originally ordered green beans but they were out, so I opted for the cauliflower. I wasn’t really a fan of it. All in all, we had a great meal here.
Art on the Mart
Looking for something free to do in Chicago? I highly recommend walking down the Riverwalk and seeing all sights from down by the river. If you are close to the Merchandise Mart in the evening, you’ll want to grab a seat across from the Mart for their nightly show called, Art on the Mart. This 4 billion square foot building originally housed some of the biggest names in retail and now puts on a lights and sounds show every evening after dark (which is 9pm in the summer). The show is about 30 minutes long and repeats itself once just in case you missed the earlier show. It was really cool and definitely a must see.
