So, you’ve got 2 days to see Chicago but you’re not sure what to do? This Chicago Itinerary and guide will give you some great ideas on what to see, eat, and do in Chi-Town if you only have a couple days!

Everytime I visit Chicago, I’m always blown away by how much this city has to offer. It has incredible architecture, delicious food, all kinds of culture, great nightlife, and the people are seriously so nice! Its kind of like the feeling of being in NYC, but with friendly Midwest people…such a great combo. I’ve created this Chicago Itinerary and guide so that if you are heading to Chicago for your first or tenth time, you have some great ideas on things to do while in the Windy City!

Of course, Chicago is a big city with tons to offer, so you really won’t even scratch the surface in 2 days, but that’s ok, it just gives you even more reason to come back for more! Read on for all my suggestions on what to do in Chicago and what I did with my girls from Babes that Wander on our first group trip!

Just a quick little intro to the Babes that Wander before we get started…Back in the beginning of 2020, myself and the four other ladies of BTW: Iesha, Elise, Greta, and Lauryn, all had a vision to create a collaborative travel group to share our unique and diverse perspectives and encourage more women to get out and explore. Of course, the pandemic had other plans, so we are so thrilled to FINALLY be traveling together! Stay tuned because we have some exciting upcoming trips planned for Nashville, Las Vegas, and more in 2022!

Just a quick heads up before we get started….we were graciously hosted by Choose Chicago, so this post is in collaboration with them and their various partners. In addition, this post does contain affiliate links, so if you make a purchase through them, I may get a small commission at no cost to you…thank you so much for supporting the brands that make my blog possible!

What is the best time of year to visit Chicago?

Ok, for me, the answer to this is pretty simple: anytime but winter! Ok, jk, there are some great reasons to check out Chicago in the winter, however, I don’t think this Socal girl can handle the sub-zero temps with that crazy wind coming off lake Michigan! The latest in the year I’ve been in Chicago was November, and that’s probably the most I could handle.

Summer is a great time to come and see all that Chicago has to offer. The city really comes alive and is so vibrant in summer. There are so many festivals (I mean, hello, Lollapalooza), tons of beautiful outdoor dining areas, and rooftop bars to enjoy a cocktail and insane views. You’ll even see people out on the river boating and kayaking. They even have a whole beach believe it or not! The only downside to summer that you should consider is the fact that it can be very hot and humid. When we were there July 23-26, and the heat was pretty intense. Just make sure to stay hydrated and keep outdoor activities earlier or later in the day.

Spring and fall are also great options to see Chicago, because you won’t have the intensity of the super freezing temps in winter or the crazy summer heat and humidity. I personally would love to come back in the fall to see the leaves change and actually get some real use out of my sweaters and boots. I may love living in LA, but I sure do miss fall on the east coast, and I know Chicago would be beautiful that time of year if fall is your jam too.

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Getting to Chicago

If you’re like me and live pretty far away from Chicago, you’ll want to catch a flight. There are two airports that service Chicago, O’Hare and Midway. O’hare is probably the one you’ll fly into, with Midway being more specifically for Southwest Airlines. Once you land, you can either take the train into town or an Uber/Lyft. I have done both in the past, if you want to save a bit of money and take public transportation like a local, do it! I always find that if you have either the Apple Maps or Google Maps app on your phone and you imput where you want directions to and choose the public transportation option, it gives you all the info you need to find your way in a new city. If you prefer to grab an Uber or Lyft, just a heads up ride share prices can be pretty steep from the airport into downtown. I arrived during rush hour and my Uber to the loop area was $80! On the way back to the airport it wasn’t as bad because it wasn’t peak hours, but it still ran me about $40. I would NOT recommend renting a car while in Chicago. Parking is always a challenge and expensive, plus you can get around the city just fine by walking, taking the train, or using ride share apps without having to deal with the stress of driving.

Getting Around

That brings me to how to get around once you’re in Chicago. Like I mentioned, driving is not recommended. If you stay in the main loop area of Chicago, there are so many of the main sights that are in easy walking distance. We walked a ton during our trip. There is also the “L” which is the train system in Chicago. You can buy a Ventra card and add funds to it if you plan on using the train a lot, or just pay per trip. Additionally, you can use Uber or Lyft to geet around as well as various e-scooter brands that are around town. Chicago also has a bike sharing program called Divvy. A single ride will cost you $3.50, or you can rent a bike for the whole day for $15.

Where to Stay in Chicago

I highly recommend staying in the Loop area of Chicago. This will put you in close proximity to all the fun Chicago sights and spots you’ll want to check out. Being in this area is also safer and will allow you to walk a lot more places. On our trip, we stayed at the 21c Museum Hotel, which was the perfect spot, as it is located just one block from Michigan Avenue in Chicago’s River North area so it is the perfect home base for getting around to all the places you’ll want to see in Chicago. This hotel was so unique because it also has a modern art museum located in the lobby and on the second floor of the hotel. You can literally “sleep over at a contemporary art museum”! Most unique concept/offering ever, it is unlike any other hotels I’ve ever stayed at. I loved getting to check out all the incredible artwork from emerging artists. Even if you aren’t staying at the 21c Museum Hotel, you are free to step in and check out the art they have on display. The hotel also hosts a tour every Thursday at 6pm.

21c Museum Hotel Chicago just announced several brand-new hotel packages perfect for this summer including the Unlock Chicago Package, Art Lovers Package, Pet Package, Girls Getaway Package, Love is Love Package. There’s something for everyone! Head here to book your stay!

Here’s some snaps from my room….I loved the chic modern decor! The room was really spacious considering it is in downtown Chicago, and had plenty of room with two queen beds, which were so comfortable. I loved the huge window and the view, and the fact that the room had a Nespresso…I am one of those people that needs a GOOD cup of coffee in the morning, if you know what I mean!

My Two Days In Chicago Itinerary

Let’s get to all the fun stuff! If you are only going to be in Chicago for a couple days, here is a fun-filled Chicago itinerary for you to save for later when you visit the Windy City! I say that this is a 2 day Chicago itinerary, but in reality, we were there from Friday afternoon to Monday afternoon, so we had two FULL days, give or take.

Chicago Itinerary Arrival + Full Day 1 (Deep Dish Pizza, Pilsen, Architecture Tour)

I arrived in town a bit later than the other girls of Babes that Wander, so they got to do a lot more exploring on the Friday we all got in. I was super bummed to have missed going with them to Three Dots and a Dash, which is a speakeasy Tiki Bar in the River North area of Chicago. This place looks so much fun, I really love a good tiki drink, especially in the summer time. If you want to dive deeper into learning about different rums and the processes around creating classic and also modern takes on tiki cocktails, make a reservation at their Bamboo Room!

For dinner that night, we had to start our Chicago trip off with deep dish pizza. There’s definitely a debate among Chicagoans about where the best deep dish pie is served, but we decided on Lou Malnati’s as they are considered the oldest family name in the Chicago pizza game. They make each pizza from scratch using the same time-honored, secret family recipe for a crust that is so buttery and flaky. The ingredients are super fresh and you can tell in all the amazing flavors of their handpicked, California vine-ripened tomatoes and fresh mozzarella cheese that comes from the same small dairy farm that has supplied Lou Malnati’s for 40 years. Make sure you come hungry, because deep dish pizza is super filling, I only had one slice. Between the four of us, we were able to split one large deep dish pizza no problem, AND have leftovers to bring to our 5th member, Elise, who got in later. Let me know down in the comments below who you think is the best deep dish pizza in Chicago!

After dinner, we decided to walk to the Chicago theater to get some photos. If you’re wondering where the most instagrammable places are in Chicago, then this spot is up there on that list! We came around 9pm and got some great shots. Of course, you can come and actually see a show here as well! Check out their awesome upcoming lineup which includes some of my favs like Neil deGrasse Tyson, Future Islands, Rufus Wainwright, Hasan Minhaj and more!

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Now, onto our first full day in our Chicago itinerary….

Snapping Photos at the Bean + Millennium Park

We woke up at about 6:30 to get ready and walk over to Chicago’s famous Bean, or the “Cloud Gate” as it is officially called. This is probably one of the most iconic spots in Chicago, so if you want to get a great photo in front of the Bean without approximately 1 million other people in your shot, you gotta wake up early. This is a rule that really goes for anywhere you visit where there is a super popular/touristy landmark. Yes, you’ll lose a couple Zzz’s momentarily, but that bomb picture you took will live forever! We arrived at the Bean around 7:30 am and there were only a handful of other people around, so we got tons of great shots and got to appreciate this massive sculpture by Anish Kapoor without the massive crowds. This fascinating sculpture is made up of 168 stainless steel plates that are welded together to form this seamless bean shape. You’ll definitely want to snap some fun reflective pics, maybe even get a bit wild with your poses for a really trippy shot! Be careful though, I have many years of ballet and figure skating to thank for this back bend 😉

If you are enjoying this post, make sure to check out my San Diego Travel Guide!

Another great spot to snap photos in Millennium Park is Wrigley Square, which you can find on the northwest end of Millennium Park. This fountain surrounded by a semicircle of paired Roman Doric-style columns makes a gorgeous backdrop for photos. Just make sure to be careful not to fall in, although with the summer heat already picking up at 8am, I almost wished I lost my balance!

But first…err….second…coffee!

On our way back to the hotel to freshen up before brunch, we stopped into Venteux for some coffee and a croissant to hold us over till brunch….being fabulous and shooting insta-worthy content can really get your appetite up! This French brasserie is attached to the Pendry Hotel on Michigan avenue, and it is as ‘grammable of a location as you can find. I love the tropical wallpaper that covered the walls all the way up to the high ceiling, and their latte art is on point. I definitely want to come back on my next trip and try out their oysters and cocktails during their happy hour as well!

Brunch in Pilsen

At 10:30, we called an Uber and headed out of the downtown area to Pilsen, a neighborhood on the Lower West side of the city. While in Chicago, I highly recommend getting out of the main loop area and adding a bit of exploring some of Chicago’s other distinct neighborhoods to your Chicago itinerary. Pilsen has always been a sort of gateway for immigrants in this city. In the late 19th century, this neighborhood was home to Polish, German, and Italian immigrants. Over the years, its demographics have changed and now it is predominantly populated with people of Mexican descent. Upon arrival, we were starving, so we stopped into Pilsen Yards for some brunch.

Pilsen Yards is a bar-centric and music-driven hangout in the heart of Pilsen with an open air vibe and one of the best patios in the city. Executive chef Carlos Cruz’s menu of inspired latin street food, from tacos to ceviches, hummus to carne asada is plated up next to a mezcal, tequila, & whiskey charged bar program from bev director Lance Bowman, and it’s all on the cheap. I love the vibe here, it feels so light and airy, and the walls are covered in a rotating collection of local art, so this space truly feels like an extension of the neighborhood surrounding it. On weekends, they have live DJ sets and I really was vibing with all the tracks the DJ played while we were there. From the cocktails, I loved the Mango Mango Foxtrot and the Last Straw, both a surprise for me since they were rum based and that’s not my normal go-to. My food rec’s from the brunch menu have to be the Pina Colada Ceviche, Chipotle Hummus, Coliflor, the Sweet Corn Tamales, and the Concha Toast.

As we wrapped up brunch, myself and the other Babes that Wander got to take a peak inside The Alderman, which is a small speakeasy inside of Pilsen Yards. This space is cozy and intimate…it only seats 16 people, so make sure if you want to check this spot out, you make a reservation in advance. It would be a great spot for a nightcap, date night, or even for a small private event. The beverage program comes from Chicago’s most award-winning mixologist, Lance Bowman, who rotates half of the cocktail list every two months while perfecting the art of tradition with his riffs on American classics, staples of the cocktail list at The Alderman.

Walking Tour of Pilsen

After eating way too much food at Pilsen Yards, we met up with Chicago Greeter tour guide Sherry for a free walking tour of Pilsen. Chicago Greeter is an organization that offers free walking tours with local volunteers all over the city. They are part of the larger International Greeter Association that offers free walking tours all over the world. Let me repeat, Chicago Greeter tours are FREE, and they can accommodate up to six guests. Tours can be offered in over a dozen different languages and are super fun, informal, and you are sure to learn some really interesting facts that you’d never find in a guidebook. If you want to book a tour, make sure to register 10 days in advance of your arrival in Chicago so that a tour can be arranged for you. If you’re looking for budget friendly options for your Chicago itinerary, definitely consider one of these tours!

The first thing you’ll notice as you arrive are all the colorful murals almost everywhere you look. Pilsen is a really hip, up and coming neighborhood with a lot of artistic talent and delicious places to eat. It isn’t surprising that Forbes named it one of the “12 Coolest Neighborhoods around the World.” In Pilsen you can savor delicious Mexican cuisine, explore their endless street art, and shop some really quirky boutiques, well-curated vintage stores, or check out the National Museum of Mexican Art.

Pilsen is also home to one of Chicago’s most treasured music venues, Thalia Hall. This structure was originally the town meeting hall and was modeled to replicate the Prague Opera House. Today, it is a multi-venue space that includes Thalia Hall, Dusek’s, The Tack Room, and the Punch House. Its a great place to catch an indie band or comedian set, grab some food or some drinks. We didn’t get to try any of these spots as we were in Pilsen earlier in the day, but we managed to get the attention of a manager who was just coming in, and he let us step inside and check out Thalia Hall. If you’re able to catch a show here while visiting Chicago definitely do!

Chicago Architecture Tour…my favorite activity on our Chicago itinerary!

After our tour of Pilsen, we headed back into downtown to freshen up and get ready for our Chicago Architecture Foundation River Cruise aboard Chicago’s First Lady Cruises. While we had nothing but hot, full blast sunshine for the first half of the day, the weather quickly changed to cloudy and then all out downpour. We almost thought we would get rained out of our boat tour, but the rain let up just in time for us to head down to the Riverwalk to board our tour. This is one thing to keep in mind when in Chicago, the weather can change very quickly, so make sure to check the day’s weather forecast and carry small umbrella with you if you need.

This was my second time taking a Chicago architecture tour, and even though it did rain off and on during our cruise, its still one of my favorite things to do while in Chicago. This 90 minute cruise is so relaxing and its an amazing way to see the city and learn fascinating facts about the different schools of Chicago architecture as well as the people who played a part in building this beautiful city. Being the birthplace of the skyscraper, Chicago is rightfully pretty obsessed with their architecture and you will be too after you disembark from your tour. When onboard, you can choose to sit up on the open air decks for the best views of the city, or you can sit on the first floor in the indoor lounge. If you want to partake in a beverage, there is a bar on board where you can purchase sodas, juice, cocktails, beer, wine, and snacks.

Chicago’s First Lady Cruises is definitely the tour company you want to book with…they are the #1 tour of the city based on TripAdvisor user reviews, so you definitely have to add it to your Chicago itinerary! This tour is helmed by passionate volunteer docent tour guides who are super knowledgeable about the city and its history. It is the only tour that is partnered with the Chicago Architecture Foundation and a portion of each ticket sale goes to architecture education provided by CAF. Head to 112 E. Wacker Drive, Chicago’s Riverwalk at Michigan Avenue and Wacker Drive (SE corner of Michigan Avenue Bridge), and look for the blue awning marking the stairway entrance down to the Riverwalk.

Dinner at Girl and the Goat

After our tour, we were definitely ready for dinner! One spot that was on all our lists to try while in Chicago was the Girl and the Goat, a Chicago favorite by Chef Stephanie Izzard. Their menu features bold, flavorful dishes inspired by cuisines around the world and are meant to be shared family style. The service here was incredible, our server was incredibly knowledgeable and everything he recommended was fantastic. Their menu features wines from around the world from small producers a rotating list of craft beers, and delicious cocktails created by their bartenders.

Chicago Itinerary Arrival + Day 2 (Chicago Beaches, Art Institute, Millennium Park, Skydeck)

Brunch at the Beach

Ok, day 2 of our Chicago itinerary brings us to start things off at the beach! When I arrived at Chicago’s North Avenue Beach, I was a bit shocked….I know that this is a lake but it really felt like a real beach! If you’re visiting Chicago during the summer, its definitely worth a trip down to this popular beach to catch some sun and dip your toes in Lake Michigan. If you’re looking for a fun spot to hang out near the water, look no further than the Oasis Shore Club. This is a fun day club steps away from the sand with a beautiful view of the beach. Shore Club offers an experience rivaling those on some of the best beaches in the world. Grab some drinks and food in their indoor, climate controlled space featuring huge floor to ceiling windows, or make a reservation for one of their roomy cabanas outside on the sand.

Shore Club’s cocktail menu offers up tons of fun tropical inspired drinks, and they have tons of fun frozen drinks, including a whole frozen drink flight where you can sample them all. I got the froze and I gotta say, it was one of the best froze’s I have had recently, and I do consider myself somewhat a connoisseur in this area. This would be the perfect spot if you’re on a trip with your girls and me and my girls had a blast!

The Art Institute of Chicago

You can’t have a Chicago itinerary without including a trip to the Art Institute! The Art Institute of Chicago is one of several world class museums in this city, and it is on par with some of the great museums in the world. Here you can view some of the most famous works by impressionists like Monet, Manet, Renoir, and more. The Art Institute also has an extensive modern art wing with works from Picasso, Warhol, Rothko, Pollock, and many others. I recommend giving yourself at least 3 hours if not more to take everything in!

We happened to visit the museum when the Obama’s portraits were on display. If you can see this exhibit while it is in town, it is not to be missed. The exhibit talks about how Barak and Michelle met and started dating in Chicago and also gives more info about the two Black artists who were commissioned to paint their portraits.

Another incredible exhibit we had the pleasure off seeing was the Bisa Butler exhibit. Bisa Butler is a portrait artist who uses fabric and quilting in the most virant combinations of fabrics to celebrate and reimagine the narratives of Black life. Butler choses to work with fabric specifically because it is a marginalized medium. I was totally in awe of every single piece and how she is able to capture emotion and character using fabric.

Checking out Millenium Park…again!

After a trip to the Art Institute, it makes the most sense to explore Millennium Park because they are right next to each other. We entered the park near the Crown Fountain, which consists of two 50-foot glass block towers at each end of a shallow reflecting pool. The towers project video images from a broad social spectrum of Chicago citizens, a reference to the traditional use of gargoyles in fountains, where faces of mythological beings were sculpted with open mouths to allow water, a symbol of life, to flow out. On a hot day, you’ll see a bunch of people splashing around in the shallow water between the two fountains, so if you have small children, this is a great place to bring them.

Just a couple steps away, on the same end of the park is the Lurie Garden, a much more tranquil and peaceful area of Millennium Park. This quiet retreat from the hustle and bustle of the city naturalistic plantings and ecologically sensitive maintenance practices to create an urban oasis for city dwellers and wildlife alike. In the summer, you can see an abundance of blooming flowers with butterflies and bees making their rounds.

Shopping on the Miracle Mile

In true blogger fashion, we ran out of outfits to wear….I know. Crazy right? Thankfully, being that we were super close to some of the best shopping Chicago has to offer on the Miracle Mile, we had our pick of all the stores we could want! Along Michigan Avenue, also known as the Miracle Mile, you’ll find everything from luxury shops like Burberry to fast fashion like H&M and Zara. You can literally shop till you drop here, it is the fashion lover’s paradise. Make sure to give yourself some time on your Chicago itinerary to do a little shopping on this famous street.

Skydeck at the Willis (Sears) Tower…a Chicago Itinerary Must!

No trip to Chicago is complete until you’ve gone sky high to the top of the Willis Tower and visited Skydeck Chicago! The Skydeck underwent a ton of renovations since I was last here in about 2012 and the improvements they made are so cool. You start off downstairs in the newly added interactive exhibits that help you learn about Chicago’s history and feature tons of fun photo opportunities that are so Chicago…like sitting on a huge deep dish pizza, riding a simulated “L” train, or getting on stage at Second City.

Be prepared for that elevator ride up…it goes fast so you may experience some popping in your ears!

Once you arrive on the Skydeck, you are rewarded with some of the best views of the city. You absolutely MUST get a picture out on the “Ledge,” which are four glass boxes built out from the building itself. Stepping out onto that glass floor 103 levels above the ground is such an adrenaline rush!!! To get out on one of the ledges’ you have to line up and wait your turn. Our wait was about 30 minutes long. Once its your turn, your whole group has 90 seconds to go out on the ledge and take pictures. That’s it! So make sure if you want to get an epic shot, you game plan before hand so you can use your time the most efficiently.

Dinner at Sunda

For our last dinner in Chicago, we checked out Sunda New Asian. I don’t often describe restaurants this way, but this restaurant is sexy. It is grown. It is chic. Their menu is inspired by a lifetime of culinary and culturally immersed travel throughout Southeast Asia. Sunda’s concept seeks to celebrate the beautiful fusion of intermingling cultures found on the Sunda Shelf, a landmass, today submerged under shallow seas, that was once surrounded by the many different countries and cultures we celebrate at Sunda today like Japan, the Philippines, Indonesia, Thailand, China and more. At Sunda, they take classic Asian dishes and reinterpret them in a modern way for an experience that is truly special. I found the portion sizes to be really generous for a restaurant of this style, and because we ordered family style, we all got to try a little bit of everything.

More Chicago Itinerary Suggestions/Ideas

Here’s a couple more suggestions of things to add to your Chicago itinerary that we either didn’t get to do or I have done on past trips that I loved…

Catch a Cubs Game at Wrigley Field

If Chicago loves their architecture, they love their Cubbies even more. Catching a baseball game at Wrigley Field, one of the oldest and most loved baseball fields in the US, is an experience I’ll never forget, mostly because we were FRONT ROW right on top of the dugout. Epic. Grab a beer and just sit back and enjoy the game. If they still carry it on tap, make sure to try local brewery Goose Island’s Sophie, which is my favorite beer in the world. Check the schedule and get tickets here.

Grab drinks at a rooftop bar

In the summertime, heading to one of Chicago’s rooftop bars is a MUST. This was something we didn’t get to do but I will definitely put on my future Chicago itinerary. Cindy’s Rooftop in particular offers fantastic views of Millennium Park and the Bean from above. Make a reservation well in advance because this spot is popular!

Starbucks Reserve Roastery

If you’re a coffee junkie like me, you’ll want to check out Starbucks Reserve Roastery on Michigan Avenue, which is the world’s largest Starbucks. This is a four story Starbucks that has a coffee shop, cafe, cocktail bar, store…I mean what is not in this place? Be aware that they are only letting in so many people at one time due to covid, so there is always a line of people waiting outside the door to get in. We attempted to check it out, but the wait was simply too long. If you can stick it out and you love coffee that much, try one of those coffee cocktails for me!

Chicago FAQ’s

What should I pack for a trip to Chicago?

To this question, I would say it really depends on the time of year. I think regardless of what season you visit in, comfy shoes are a must. There are shoes you think are comfy but they’re actually not when you put them to the test walking several miles in a day. Trust me, I know first hand as I have given myself plenty of blisters while walking around the city. If you are coming in summer, bring clothing that is lightweight and breathable, preferably items made of cotton or linen work best in the hot humidity. In the winter, be sure you bring your warmest coat and plenty of warm sweaters, a scarf, gloves, and beanie.

I also think its wise to bring an external battery charger or grab a phone case that will charge your battery. This is a great powerbank, and if you want to go the phone case route, check out this one. You’ll be on your phone a ton documenting your trip and also using your navigation to find your way around, the last thing you want is your battery to die midday.

Is Chicago Safe?

I feel like a lot of people ask if Chicago is safe, and I feel like as a whole, it is. Like anywhere else, there are neighborhoods to stay away from, and certain areas to not venture into at night. Being aware of your surroundings is key and knowing where to be and where not to be. I will say, stay super vigilant with your belongings especially in crowded, touristy areas as petty theft can happen. I had my purse stolen from me last time I visited after I set it down at a club and turned my back for literally 2 seconds. It sucked. Just be aware and don’t let your valuables out of sight.

Is 2 days in Chicago enough?

Two days in Chicago is really not enough, but you can get in a lot of awesome things in those two days due to the fact that a lot of Chicago’s main attractions are so close to each other. Plan out our trip as efficiently as you can by grouping activities on your Chicago itinerary by their proximity to each other. If you don’t get it all in, hey, even more reason to come back!

Does Chicago have travel restrictions?

Currently, Chicago does not require a quarantine nor does it have travel restrictions to domestic travelers. At the time of our visit in July 2021, there was not a mask mandate, so masks were optional unless traveling via public transportation, in an Uber, or at the airport.

I hope this Chicago itinerary was helpful! Comment down below and let me know if there are any iconic Chicago spots I forgot so others can consider that for their trip! Again, big thanks to Choose Chicago for hosting our first ever Babes that Wander trip! I can’t wait for many more!

Looking for some more fun domestic vacation ideas? Check out this post on Rushcreek Lodge at Yosemite!

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