How To Live It Up In Chicago For a Long Weekend Without Breaking The Bank

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Every time I run into my friends they always say to me something about how much I travel and where is the next place we are off to.  Secret over here, I have so much PTO saved up because we always travel long weekends and are back to work on Monday. Yes those Monday’s are pretty rough but I’d rather save up those vacation days to keep for these fun dashes!  Chicago is definitely one of my top places we go every year for our birthdays and take advantage of the long July 4th weekend.  The best part of Chicago it is such an easy city to navigate and this past weekend we did not take one cab.  I will also give a disclaimer I clearly do not live or have not lived in Chicago this is an outsiders view so if any locals have any additions please feel free!

Chicago Guide on a Budget

My How To Guide To Live It Up In Chicago Without Making Your Wallet Cry

tie dye dressSomehow these colors worked for the 4th right?
Dress sold out similar here///handbag here///gold belt similar here///Watch sold out similar here///Tory Burch cuff bracelet here///Ray Ban Aviators here

Take The Train

The airport is a direct shot on the train into the city.  We flew up Southwest which brings you into Midway which is a shorter train ride into the city from the Orange line, just about 30 minutes.  On the way back we flew United which flies into O’Hare.  O’Hare is at the end of the blue line which is roughly 45 minutes into the city.  Total fare is $2.25 for each person.  I would say $5 is way cheaper than a cab ride.  Bringing our bags onto the train were no problem.  You can easily route your way using this. We were staying in the River North section so we got off at Clark/Lake which is a major hub and walked the three blocks to our hotel.  Last year we took the train out into the Lincoln Park area to go to the Goose Island Brewery Tour it was a fabulous way to spend an afternoon especially with all the great restaurants and shopping out that way.  After we got from the airport we never took a cab and walked the entire time which brings me to my next point.Chicago TrainHere I am riding the train safe and sound (in a hideously unflattering shirt but that is besides the point).  Peep that blue polish from yesterday’s post.  Wasn’t joking how much I loved it!

Pick A Hotel Close To All The Action

We stayed in the River North section.  It was two blocks off Hubbard where all the bars are and close to Illinois where a lot of the restaurants are that we like.  It was walkable to everywhere we wanted to go.  I found the hotel using Priceline, they had a coupon code (naturally).  I picked the stars I wanted and location and got a great hotel.  When we arrived I asked for any available room upgrades.  We ended up getting on the club level which had free breakfast, hors d’oeuvres, water and a Nespresso machine.  He also threw in the internet all for a very reasonable upgrade price (like less than a lunch out kind of range).  We were also two blocks away from the Bloomingdale’s home store so we definitely checked out the new Nespresso flavors……daily ;-)  The very sweet concierge also sent up a bottle of wine with a cheese and cracker tray (like how did he know how much I love??) for my birthday.

(pretty much eat four of those a day while I was there)

Go To All the High End Places…….For Lunch

Gibsons for dinner……yeah right.  Gibson’s for lunch absolutely.  I love high end places for lunch because they usually have menus you would never see for dinner.  Like their spicy Lobster Cobb salad.  It is perfection and $14.  Pair that with a nice glass of wine and plenty of people watching…..that is the way to do it.

Revlon matte lip balm also from yesterdays post

Oh and Mark loves going to David Burke’s Prime House for their Steak burger…..I got the regular burger, so good!  Honorable mention to Ruth Chris for Happy Hour but it was only during the week day, that ahi tuna was amazing.

ruth chris

Check Out The Deal Sites

Groupon, Living Social, Travel Zoo…..all of them.  Check out the deals.  If anything it will give you good ideas of places or events to check out.  Like hello Counting Crows concert.  Just make sure to check the fine print some of them don’t work for weekends or holidays.

All those swanky rooftop bars

Go during the day.  You will get an amazing view of the city but won’t have to be bullied into buying bottles to reserve a couch or table space.  Plus you will have the place to yourself to sit and enjoy an adult libation while catching up with your company.  My favorite of the trip was the Ivy Hotel.  Thanks Katie for the suggestion it was the most amazing view and friendly staff!  Our girl Amelia was beyond sweet and took like 15 pictures for me without even asking to change the angles and poses….she just got me ;-)

Ask The Locals

I sent out a mass email to the locals in the area asking their opinions about all the places we needed to try.  That way we stayed out of the tourist traps that are usually very expensive.  Thanks so much to Stephanie and Katie for your fabulous recommendations!

Don’t Shop There

I mean you can window shop and have a blast cruising up and down Michigan Ave.  Unless the deals are amazing…..the 10% sales tax is craziness.  Or if you shop at Nordstroms have them ship it to your house so you won’t have to pay their taxes.  Or do like I do…..ship everything to my sisters house in New Jersey.  The few good parts about Jersey, no tax on clothes and they pump your gas for you.

Bring Lots of Small Bills

Tipping is greatly appreciated and seriously when someone helps you with a service it is expected.  Then you can also hit them up for their local knowledge.  Or just by being genuine and nice you may wind up on a high level floor with a gorgeous room of the city.  A great tip I learned from my sister before traveling make sure to go to the actual bank and get lots of different bills, ones, fives and tens. Instead of the 20’s you get out of the ATM which seem to magically disappear when no one has change.  That way you will have small bills for tipping and you won’t blow through 20’s as easily.



Live It Up

I mean we all work hard and you can’t be buried with it.  So if you want to sit on the rooftop drinking a fabulous glass of wine or those shoes you had an eye on might just magically be making it to your sisters house in the next week…..go for it.  You will always think of that great trip when you pull them out and it will make staying those extra few hours worth it when you can really enjoy yourself on vacation.

Did I miss anything?  What are your insider trips when you travel?  What is your favorite place in Chicago to hit up when you get there?

Honorable Mentions


We go every year for my birthday there.  The sushi is definitely expensive but good.  Mark ordered the short ribs and I was insanely jealous of his order.

Glazed and Confused

I mean I am still dreaming of that red velvet donut.  Also if you show their your ID on your birthday you get one free!


Make Sure Not To

Have a random hippie couple take your picture…..they will take it shooting you from the ground up.  Let’s be honest nobody looks good that way unless you are Christina Aguileria in the Genie in the Bottle video.  Then those said hippies will ask you to take a picture of them with their digital camera because they don’t have “a fancy phone like you“……then they proceed to take out a Zack Morris size digital camera and then insist on putting it on nigh time mode.  Don’t worry.  I’ll wait.

I also wanted to thank all of you for your incredibly sweet and thoughtful birthday wishes!  I have definitely accomplished a lot in my 20’s and I can’t wait to dive into these 30’s and see where it takes me!  xoxoxoxo

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57 responses to “How To Live It Up In Chicago For a Long Weekend Without Breaking The Bank”

  1. Welcome to the 30 club!! You started your off right! Please tell me you bought those shoes!!??! I’m a fan of buying yourself a big gift for a big birthday. Feels pretty dang good! And I love all of your tips, I think I need a little visit to Chicago now. Happy Birthday again!

  2. Becky M says:

    We may be going here in August so I’m glad you posted this!!

  3. All great tips girl! LOVE your 4th of July outfit! You are totally rocking that maxi with that belt. Amazing! Oh I totally went out and bought that blue polish from your post yesterday. I love it! And I want one of those donuts… so bad. Did you get the shoes?!? :)

    <3, Pamela

  4. These are great tips for ANY city you’re going to!! I’m actually going to use some of these for our trip – especially the lunch and rooftop bar suggestion!! I love that red dress you’re wearing that the hippie took of you haha!! I am craving a donut now…

  5. welcome to the 30s! way better than the 20s if you ask me and like fine wine, we just get better with age.

    we always try to walk or talk public transit when getting around. that’s what we do in vegas – the bus is only like $2 and it’s the most hilarious thing ever because all the drunk people get on and make fools of themselves hahaahah!

    Vodka and Soda

  6. Now I want to go to Chicago! Also, those donuts (ok, all the food!) look delicious!!

  7. haha i love this post! chicago is a great town and you’re right – really no need for cabbing it which is great. and the food – so good! love your list of what not to do as well – hilarious! xo

  8. Ashley says:

    Awesome tips! We’re heading there next month for a bachelorette party and keeping these in mind! You look beautiful and I 100% need that donut!

  9. Rebecca Jo says:

    That birthday donut is awesome.
    I love the idea of visiting the swanky for lunch! So genius!

  10. It looks like you had a great time in Chicago! Ah, how I miss living 20 minutes from that city. :) Your tips are great for any traveler to any city.

  11. Hope you guys had an awesome trip! I love your sunnies!

  12. Sounds like you had a fabulous trip and birthday! Love all your great travel tips and outfits! Those donuts look so good!

  13. Mree says:

    Looks like it was a great trip!! I so want to visit one day!! Ok, I so love that they pump your gas in New Jersey!! Wish more places would do it for you. ha!

    Best, Mree

  14. awesome! We’re going Labor Day weekend for MFD’s birthday (I’ll be sure to take him to get a free donut)!

  15. such awesome tips! i went to chicago for the first time on business and definitely broke some of these rules. i hope to go back!

  16. Great tips and recap of your trip. Looks like you had a great time!

    ~Ashley @ A Cute Angle

  17. Not surprisingly I am obsessed with your entire wardrobe on this trip! It looks like you guys had such a great weekend! We have been on the fence about a Chicago trip sometimes in the near future because my husband has never been! Growing up we always drove or took the train, so your tips about what airports are helpful!

  18. Krystal R. says:

    Great tips. My friends always ask me the same thing because Im always off to somewhere. You can travel on a budget and have a blast!!

  19. Looks like an awesome trip! Lots of good food and views makes for a great vacation!

  20. Kristen says:

    yayyy thank you! i wish we could take the train, but we are driving, boo! which also means we have to park, double boo.
    and omg going to the high end places for lunch? genius. i was just starting to think there is no way my husband will let me / want to go to an expensive place for dinner, he just wont. sigh. but i want to live too! haha. so, besides the sushi place, where did you eat dinner? those doughnuts look beyond amazing. yum. and now i totally want to go to the rooftop bar during the day, you’re so smart!!

  21. yahh! im so glad you had a good time! and you are totally right about taking the L into the city– SO much cheaper than a cab! and faster during traffic. i also love the tip about going out to nice places for lunch, it’s SO much cheaper! xo jillian – cornflake dreams 

  22. Great tips, especially love the high end places for lunch! I loved Chicago when I went last year, I’ll definitely want to return :)

  23. Going to the fancy places for lunch is such a good tip!

  24. MarlaJan says:

    Eeeeeeeeeeeekkkkk!! This made me so excited and will most definitely be referring to this in September! Roof top bars during the day, yes please. Glazed and Confused.. YES PLEASE!!!! You look amazing in that tie dye dress. I bought about 4 more dresses over the weekend (in NJ, where’s there NO tax on clothes!) and I thought of you! <3

  25. Tracey says:

    I am going to bookmark this post! My husband and I really want to visit Chicago and after the wedding we have limited funds and vacation time left!!

  26. love that first maxi dress you’re wearing! happy belated birthday! i will have to bookmark this in case i ever get back to chicago :)

  27. Stephanie says:

    So glad you had a good time! Birthday donuts are one of the highlights of my year :)

  28. Looks like a REALLY GREAT TIME! I really enjoyed seeing many of your adventures on IG! PS, these are all really great tips that can be applied to any big city one travels to! Great post! :)

  29. what an awesome and informative post!! looks like y’all had such a fabulous time and I love LOVE what you wore! I’ve only been to chicago briefly and I’d love to go back !

  30. Jen says:

    So jealous of your trip! It sounds amazing! The next time I go to chicago I am dragging Steve around to all of these places. We always go to the same spots! :(

    Ps LOVED your outfit in the picture at the rooftop bar.

    xo, Jen

  31. I totally forgot to tell you I bought some mirrored aviators in Hilton Head and thought of you!!
    Great tips!

  32. even though we both live in chicago, these tips definitely help us locals who don’t want to have to splurge to have fun in the city all the time, looks like you had a fun trip here!

    Brittani and Katie

  33. THAT HIPPIE COMMENT THO. I’m dying. Mostly because I hail from Minneapolis, and know EXACTLY the type of upper-Midwestern hippie you’re referring to :)

  34. I love this! I have always wanted to visit Chicago, and it looks like you know how to do it right!!! Looks like you had a fabulous time! I am going to go dream about those donuts now!

  35. Great ideas, these can apply anywhere! I hadn’t really thought about doing fancy LUNCHES, genius!

  36. I love that so much of Chicago can be seen on foot. Eating at the fancy places for lunch is such a great idea! Sounds like you had a great trip!

  37. The lunch tip is genius! And then I’m hoping there is a Chick-fil-a for dinner ;) You did your 30th right! Cheers, pretty!

  38. Great tips! I esp love the suggestion of going to fancy spots for then you don’t break the bank or eat too much and want to sleep post-meal, instead of live it up!

  39. Your trip looks amazing – those are some pretty great tips! We pay 13% tax on everything, it’s killer. I always go crazy on the shopping when I go somewhere in the states that already has cheaper prices AND no sales tax. It’s like Christmas!

  40. Tami says:

    HAHA the hippie with the digital camera. my mom still carries one with FILM! i’m loving everything you’re wearing on your trip

  41. Wow, that looks like an awesome weekend! I have become a big fan of the weekend getaway. It’s the only way I can afford to take my kids anywhere… short and sweet. No time for week long vacays or budget either. Great tips… I am learning all kinds of good stuff from you!!!

  42. alyssa says:

    Looks like SUCH an amazing trip!! You are also seriously the travel master. Next time I take a vacation will you plan the entire thing for me?? thanks ;)

  43. Saving this for my Chicago trip in two weeks! And I am like you- lots of long weekends and few long weeks. Hence my weekends in Jersey, Chicago and Tampa within a month!

  44. So glad you guys had a good time!!! And isn’t the Ivy amazing?! We had dinner and spent the night there for my bachelorette party! Yay for an awesome room upgrade and I’m pretty much drooling over the Glazed and Infused donuts. SO delicious!

  45. Glad that you had a nice time here. I love Sunda and recommend it to a lot of people. I haven’t been to Glazed & Confused but I’ll have to remember that free birthday donut! :-) I also take the bus and train everywhere here. Or I walk. It definitely makes things more affordable. :-)


  47. These tips are amazing! I’m planning a trip to NOLA in two weeks and I’ve been planning on a lot of these! Especially Groupon and going to the fancy places for lunch! It’s crazy how many lunch specials they have! So glad you had an awesome birthday!!

    <3 Shannon

  48. Glad you had a good time! Looks like fun.. can’t wait to visit Chi town one day and I will remember your tips!

  49. Myra says:

    Uhm, how do you get more & more gorgeous in every post?! And your clothes. Get outta here. I need to come raid your closet. Not that it matters at all that I’m about 7 inches or so shorter than you or anything…right? Glad you had a fabulous time in Chi town! I love that place!

  50. Damn girl! You have shit allllll scouted out! I’ve never taken a trip to Chicago or even planned a trip like it! I love all your tips and suggestions!! Looks like you had a great weekend and birthday! I love all your outfits (of course) and all of that food looks amazing!!! I totally agree with you about taking long weekends and saving up the PTO! I do the same thing and people always ask me if I even work anymore. Haha. It’s all about scheduling ;)

  51. Wow! What an amazing birthday! Happy 30th Amanda! Looked like a great time in Chicago! I’ve only ever been for work so I need to go for fun sometime. Thanks for sharing!

  52. Happy belated 30th girlie!! 30 looks good on you pretty lady!! I love these tips and was cracking up about the “few good things about Jersey.” Bahaha that’s the truth and I live there!

  53. Em says:

    Happy belated birthday!!! You were in my neck of the woods girl!!! My fav rooftop bar is at the Wit! Looks like you had a fabulous time and all of your maxi dresses?! Ummm I need them all hahha.

  54. LOVE BIRTHDAY MONTH! Cannot wait to see more of the engagement photo shoot! Thanks for hosting…I want to say I will do the arm video workout but I’m scared! I do need some serious arm work…I’ll keep you posted. XOX

  55. I’m so glad you had fun in Chicago! Those are great tips – I definitely love and appreciate the public transportation here and tourists definitely don’t seem to utilize it enough!

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