Weekend Travel Guide: Chicago

TAKE ME BACK TO CHI TOWN!

It’s a city I’ve never been to before and I’m so thrilled I was able to experience the Windy City for 2 1/2 days; definitely wish we had one more full day to embrace all it has to offer!

HERE’S A RECAP OF HOW WE SPENT OUR GIRL’S WEEKEND TRIP!

TRAVEL DETAILS

This was a very easy trip to take over the weekend & I definitely recommend it to anyone who’s never been! We booked our 1 hour 45 minute flights in mid-April – early Saturday morning departure to Chicago and late Monday evening arrival in NYC. Our round trip flights were about $242.00 – one way: $100 each + taxes/fees.

*Keep in mind, we had specific times we had to leave (#workobligations) so although this looks pricey for just 2 days, I’m sure you can get a much cheaper option if you do some digging via Expedia/don’t have any strict flying requirements.


WHERE WE STAYED

One of my best & longest friends has a place in Lincoln Park, where we posted up for our two days. We’re still BEYOND thankful & grateful for the opportunity to stay in such a prime location, with the most GORGEOUS view of the downtown area.

(Image above is our view from the balcony! Image below are charming brownstones covered in ivy)

Before we had our arrangements, we scouted Airbnb for places and found very reasonable prices for the weekend. Keep in mind, Chicago is HUGE so you’ll most likely end up having to drive to most places (especially at night.) We found ourselves visiting the neighborhoods of Old Town and River North, which are two very fun spots for both day & nightlife experiences, so definitely see if there’s availability in those areas to limit your amount of Uber/Lyft travel, which you can save money on if you can find a new user promo after a quick Google on your phone.


PLACES TO GO

With so many places to see & explore, we had to spend our time wisely this weekend. Although there are many things we wish we got to experience, here are some of the fun places we took advantage of during our short weekend:

MILLENNIUM PARK – THE BEAN
We happened to visit this area during the 34th Annual Chicago Blues Festival, which made for a very enthusiastic (and overly crowded) venue! Nonetheless, we were able to easily get our touristy antics out with pictures of/reflecting off The Bean!

CINDY’S ROOFTOP
After receiving close to 10 recommendations to try out this amazing rooftop space, we couldn’t be happier we followed your suggestions! Seriously, this rooftop boasts the most gorgeous view of Millennium Park and Lake Michigan. Plus, the drinks were FAB!
Described as a hip, stylish rooftop bar/eatery at the Chicago Athletic Association Hotel with choice seasonal fare.
12 S. Michigan Avenue, Chicago, IL 60603
Reservations: Yes, Reserve.com or by phone; we easily walked in & got drinks in less than 20 min (including time waiting in line).
(First image via Cindy’s)
WRIGLEYVILLE – CUBS GAME (LAKE VIEW)
We really wanted to go to a game after checking the schedule and noticing the Cubs were playing the Colorado Rockies at home the weekend we were visiting! Our Cubs tickets were scored via Vividseats only two weeks before we left; for $100 each, our seats were pretty awesome off to the side of home plate (and thankfully in the shade on that 93 degree day!)
Even better, the Cubs won! We were told by this sweet older gentleman that we brought the team good luck. The people of Chicago – especially the baseball fans – were so polite & sweet, even to the Rockies fans. What a change it was from the borderline barbaric nature of some diehard NY sports fans…)

Even if there isn’t a game during the time you plan to visit, you should still visit Wrigleyville and see the iconic stadium – it’s so beautiful & an awesome piece of landmark history. Plus, the bars in the area are super fun to go to even if it’s not game day! I definitely suggest checking out these two hotspots:
SLUGGERS
Sports bar with second floor batting cages, skeeball & other games, along with a dueling piano bar.
3540 N Clark St, Chicago, IL 60657 (Lake View/Wrigleyville)

OLD CROW SMOKEHOUSE
Asian-influenced BBQ pairs with Southern cocktails & live country music in a large urban-chic space. AWESOME rooftop bar!
3506 N Clark St, Chicago, IL 60657 (Lake View/Wrigleyville)
(Image via Old Crow Smokehouse)

OLD TOWN
We heard about an Arts festival being held in this neighborhood, which is only a few blocks away from where we were staying in Lincoln Park, so we decided to check it out. This is definitely a place that’s charming by day and lively by night, with cute mom & pop shops and multiple grill/bar places to eat & go out to later on. We checked out the area that same evening and only were able to hit up one spot before falling asleep in our heels, but we had a blast nonetheless!
OLD TOWN POUR HOUSE
An upscale pub food & a massive beer list served in an elegant wood-clad space with a mezzanine.
1419 N Wells St, Chicago, IL 60610
(Image via YoChicago)

GOOD EATS

I think we ate 90% of the time during this trip but it was SO WORTH IT! There were so many places to try that we got recommendations for, and we wish we could’ve tried them all. Here are the spots we wined & dined:

RPM ITALIAN
52 W Illinois St, Chicago, IL 60654 (RIVER NORTH)
Pasta, steaks & seafood served in a sleek, group-friendly eatery backed by Giuliana & Bill Rancic. Fantastic dinner/drinks!
Reservations: Yes, Opentable or by phone; Note: we booked this ONE MONTH in advance, rated 5 stars & definitely meets the standard!
(First image via ChicagoNow)

BOTTLEFORK
441 N Clark St, Chicago, IL 60654 (RIVER NORTH)
New American small plates & entrees plus specialty cocktails served in a stylish, dimly-lit setting. Great for lunch/brunch.
Reservations: Yes, Opentable or by phone

TROQUET RIVER NORTH
111 W Huron St, Chicago, IL 60654 (RIVER NORTH)
Hip tavern serving creative cocktails, plus French-inspired breakfast, brunch & all-day bistro fare. Great for lunch/brunch.
Reservations: Yes, Opentable or by phone

LOU MALNATI’S
958 W. Wrightwood Avenue , Chicago, IL 60614 (LINCOLN PARK)
The place to get Chicago’s famous deep dish pizza! Multiple locations, this one was closest to our place & sat us right away.
Reservations: No, first come first serve; delivery available per location

CASTAWAYS
1603 N Lake Shore Dr, Chicago, IL 60611 (NORTH AVENUE BEACH)
Beachside party spot with patio & rooftop bar, frozen drinks, beer, bar food & weekend live music. Fun fact: this is an old ship that was converted to a great social scene!
Reservations: No, first come first serve.
(Image via Stefani Restaurants)

 

To Be Bright

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