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3 Days in Chicago {Tourist Style}


It's hard to believe that in just a nine (!) short days, we will no longer be Chicago residents.  Since our new home is only 2.5 hours away from the city, I'm sure we will be back here all the time... except as tourists!

Chicago is an awesome city to spend a long weekend (or more of course) in and a bunch of you have emailed me regarding trip planning to the Windy City.  The entertainment and dining options are endless here which can make planning overwhelming when you only have a short amount of time to spend downtown.  In hopes of helping, I thought I would put together a bit of a "weekend guide"!  Here are my favorite recommendations for 3 days in Chicago...

Lodging:  As a tourist, I highly recommend staying right in the heart of downtown -- in the Magnificent Mile/River North/Streeterville areas.  This will allow you to walk to many of the popular tourist spots and avoid those cab fares that can add up fast.  You really can't go wrong with any of the hotels in these areas but we've stayed at the Courtyard Marriott (very reasonably priced), The Drake (historic hotel) and The Ivy (boutique hotel) and would highly recommend all three.


Day 1
***I would try and arrive in Chicago later in the morning -- especially if you are driving in on a weekday. You do not want to start your trip stuck in morning rush hour traffic!  


Check into your hotel and then grab some lunch -- aka shopping fuel.  Some of my favorite lunch spots right on/near Michigan Avenue are Bub City, Big Bowl, Howells & Hood, Hub 51, Rock Bottom Brewery (with a rooftop bar!), Weber Grill and Quartino.  I know, I have a lot of favorites.

After lunch, it's time to take on the Magnificent Mile!  There are sooo many great stores and you could easily spend all day here.  I'd start on the north end of Michigan Avenue and work your way south.  Once you reach the end (you'll get to the bridge over the Chicago River), head down to State Street to check out the Chicago Theatre and some more great shopping.

Once your wallets have been emptied, pop on over to Millenium Park.  It's only a couple of blocks from the State Street shopping and you've got to take the quintessential Chicago picture with the Bean!

Now it's time to head back to the hotel to drop all those shopping bags off and get cleaned up for dinner.  Your first dinner in Chicago should absolutely be deep dish pizza!  Giordano's is widely regarded as "the best" but there is also Gino's East and Lou Malnati's.  My personal favorite is Lou's but ask anyone in Chicago and they'll give you a different answer!  All three have locations right downtown and you can't go wrong with any of them.

After dinner, I'd highly recommend grabbing a cab and heading to the Old Town neighborhood to see Chicago's famous improv comedy at Second City.  Always a guaranteed good time but make sure to reserve tickets before your trip as they tend to sell out of every show!

Day 2

They say breakfast is the most important meal of the day so don't just settle for a continental breakfast at your hotel!  Two of my favorite breakfast spots on/near Michigan Avenue are Yolk and Wildberry Cafe.

While it's still early, I would head to Navy Pier.  Navy Pier is 100% a tourist attraction and will get crazy busy so go early, right after breakfast.  It's definitely worth checking out as there are fun shops, a few amusement rides and some decent restaurants.

One thing I'd highly recommend doing while at Navy Pier is taking an architectural boat cruise.  My favorite is the Seadog -- it starts on Lake Michigan and takes you on the Chicago River which winds right through downtown.  They typically take about an hour and it's a fun way to learn a lot about the history of Chicago.

Saturday is for sports (I just made that up) so around lunchtime, head north to Wrigleyville for a Cubs baseball game!  You can either take a cab to Wrigley or you can get the true Chicago experience and take our train system, the "L".  I'd recommend taking the L because it's always an adventure and much cheaper than a cab at only $2.25/person.  You will need to take the Red Line to Wrigley which you can hop on right downtown... making things super easy.  Enjoy a beautiful day of baseball and don't forget to have a famous Chicago "dog" at the ballpark -- hold the ketchup.

After the game, it's back to the hotel to get cleaned up for dinner.  Saturday night is the fancy pants dinner!  I would head to the John Hancock building on Michigan Avenue to dine at the Signature Room on the 95th floor.  The views are amazing (seriously) and the food is fabulous.  The best part about going on this night is that Navy Pier does a fireworks show each Saturday and you'll have the best seats in the city for it.  Don't forget to make reservations at the Signature Room!!  It's super hard to get in without one.

If you aren't completely wiped out after a day of fun, check out the chocolate buffet (Friday and Saturday nights from 8pm-12am) at the Peninsula Hotel.  Yes, seriously a chocolate buffet!

Day 3

Sleep in!!  This is a vacation after all and you'll be tired from going nonstop the last two days.  Once you get moving, you'll want to do brunch.  Brunch is big in Chicago and a few of my favorite spots are Bongo Room, Ann Sather's and Zella's.

The rest of the day is devoted to exploring Chicago's museums.  There really is something for everyone... the Art Institute, Museum of Science and Industry, Shedd Aquarium, Adler Planetarium and The Field Museum.  My two favorites are the Aquarium and the Museum of Science & Industry but they're all amazing!  Take your pick.

After you get your museum fix in, it's back to the hotel for check out.  Don't forget to grab a bag of Garrett's Popcorn to snack on while you travel home!

Of course there is so, so, soooo much more to do and see but this itinerary hits some of the biggest and best things that Chicago has to offer!  Besides, whatever you didn't get to do you can just save for your next trip... because you'll definitely be back :)  Let me know if you have any questions, I'd love to help!

Linking up with Annie and Natalie

35 comments

  1. This is so amazing!! We want to do a trip to Chicago so badly and probably will next year - pinning this guide for that time!! The Ivy hotel look so nice!! Ok...so how do you feel about RPM - worth the reservation and visit when we go?

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  2. NINE days?! i cant believe it!! at least you can go back and visit! this list is making me really excited about our october trip to Chicago :) bring on da foooood (i love lou's too!) xo jillian - cornflake dreams

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  3. Love all of this! I would love to visit Chicago. It looks so beautiful there! And I'm wondering about RPM too? Is it actually good? xo!

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  4. This is FANTASTIC with our 1st trip to Chicago coming up in 2 weeks! Thank you so much gurlie! Still so sad we won't be able to meet up, but sooooo excited for you to close on your new house! :-D

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  5. This is great!! I love Chicago and feel like everytime I go there's something new to see or experience. Definitely pinning this post for future reference. And I am obsessed with Garrett's popcorn! I have ordered it online before... Much better than waiting in that line ;)

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  6. Ah this is such a great post for my trip next week! I'll only be in the city one day because we're heading out to a lake resort for 3 days so hopefully I can squeeze as much of this in as possible!

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  7. Great post! If I'm ever in Chicago (which I really hope I will be someday!) I'm definitely going to re-read this and use your tips! I definitely want to do the architectural boat tour! And I hear there are amazing rooftop bars in Chicago. And I'm grabbing at least 4 bags of Garrett's when I'm there... so good!!

    <3, Pamela
    sequinsandseabreezes.blogspot.com

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  8. This makes me want to go to Chicago badly! My husband has been for 2 bachelor parties but I've never been. I'm trying to convince him to take me to NYC for Christmas so if we go I'll try for a Chicago trip next!
    Life as I know it

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  9. This is such an awesome post!! I love visiting Chicago and next time I am out there, I am using this!!

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  10. Damn girl you hit the nail on the head! I'd say check out the LP Zoo and you're set! I think I'm going to make a rez at Quartinos for next Saturday night since we are staying in the city the weekend you are moving out of it!

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  11. This is such a complete list, girl. Perfect for three days here.

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  12. I love this! We are just about three hours from Chicago and go often but there is always so much to do! I love all the restaurant suggestions! New places to eat are the best! We found a place called Mila's (I think) last summer for brunch and loved it!! I guess I need to plan a trip! Enjoy your final days!! AH!

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  13. Oh I want to return for another Chicago trip so bad! Kristal and I had so much fun!!

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  14. Great suggestions, but I'm so so sorry I'm going to have to disagree with you about Big Bowl and Weber Grill. I would send people to more unique places, but that is just me. I'm old and have turned into a foodie haha. Navy Pier is nice to walk through before it gets crowded and if it is nice outside. The list of things to do and places to go here goes on forever though doesn't it?! Hope that you're having a great day so far too! :-)

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    Replies
    1. Haha Big Bowl might be my favorite restaurant ever!! I'm obsessed with it!

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  15. you're making me want to visit again! i went there for the first time in april & that garretts popcorn + the shopping was on my to do list. sadly i was there for work training, but i need to go back. awesome guide!

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  16. I love this so much, and it makes me even more sad that our little weekend was cancelled. I have pinned this and I am going to follow it exactly when we go back one day, I will make sure we do! Though there is no way my husband would let me shop that much, and I know - it's not even that much! I might leave him at the hotel while I shop, lol!

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  17. Being from Chicago, you summed up some of the best parts of Chicago! You made me miss the city - maybe I'll have to travel back and be a tourist one of these days.

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  18. This is such an awesome roundup! We are trying to plan a trip for February but sadly I don't trust the midwest in the winter-- otherwise I think Chicago would be one of our top choices since my husband has never been!

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  19. Whoa! Great great great tips! I have heard so many awesome things about Chicago, but have never been. Your post makes me want to visit ASAP. I'd LOVVEEE to stay in that historical hotel (I have a fondness for those!).

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  20. Love this post. bookmarked for when I finally get to go to Chitown.

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  21. Great recs! This is so helpful for our upcoming trip which will only be a few days so we need to map out an itinerary and try to fit in as much as possible.

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  22. I need to pin this - going to Chicago is a bucket list thing for me :) I want to run a race there....

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  23. Definitely will refer to this at some point! What's the best time of year to visit BTW? And no, we are not snow people :)

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  24. I recently visited Chicago for a work trip and I fell in love. I would really consider moving to Chicago, there is just so much to do! I love it.

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  25. I have been saying for a year now that I need to take a weekend trip to Chicago since I'm so close! Keeping all of the recommendations in mind!

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  26. Definitely pinning this post for when I get to go to Chicago one day! Thanks for all the helpful tips!!

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  27. This sounds like SO much fun!! I have only been to Chicago once, but I am dying to go back and take my husband!

    Nikki
    thefashionablewife.com

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  28. This makes me want to go to Chicago SO bad!! The Signature room looks amazing- I love any fancy restaurant with a great view :)

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  29. This is perfect! Pinning for my next trip there!!!

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  30. Such a great post! Chicago is a must visit place for me one of these days!!
    I have SO many of these things on my Chicago Bucket List

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  31. I love Chicago, so fun! ;)

    God bless,
    XO, Claire
    Http://www.littlemissfashionqueen.blogspot.com

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    fresh food delivery services | order desserts online in delhi

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  33. this is such a easiest recipe but too delicious, my niece is too lovingly with this recipe.
    online food delivery restaurant | fresh food delivery services

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  34. Lovely lunch today. Ordered the non veg item and was pleased by the quality of the chicken and also find nicely toasted roll, thick slices of ripe avocado, and crisp hot bacon which accompanied it. The side of fresh fruit was also generous and perfectly ripe. A very good experience. Add this to the best dining view on the island on a gorgeous Fall day, and it adds up to perfection.
    Chinese and Indian restaurant | Chowringhee Restaurant in Laxminagar

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