$63 to Chicago: Conclusion


Well that was one of the quickest trips we’ve ever taken and it was definitely one of the most fun. The idea of short trips like that are growing on me. It forces us to be more efficient in finding out what we want to eat/see/do. We’ll have plenty of time to relax the next time we go to a beach destination so we don’t mind running around exploring a very nice city.

This whole trip was spawned on a random afternoon browsing the forums and seeing a mistake fare posted. These can happen at any time so it pays to be flexible.

As always, thanks to Joann who takes about 90% of the photos on trips!

Stay Connected!

I always try to quickly share mistake fares, fare alerts, or just about any great fare with my readers so if you want to find out about these time-sensitive deals, follow me on Twitter, Facebook, or Google+!

I hope the next time something like this comes up that we can all FOLLOW THE FARE!

chicago panorama

So long, Chicago!

$63 to Chicago: Tornado Warnings & The Flight Home


Tornado Warnings

At some point during our visit to the Sears Tower Skydeck, a pretty significant storm started to roll in. While waiting on line to go up, everyone’s Verizon phone was sounding off with a crazy tornado alert.

This was actually really cool to watch from the 103rd floor. From here, we could actually see the storm clouds moving and just unloading on the city and Lake Michigan.

chicago sears tower

After enjoying the Skydeck for a while, we decided to get in line to go back down. The line for the elevators going down was worse than going up!

We found out that the delay was because they discontinued the use of the 2 main elevators due to the storm and high winds. Everyone was being shuttled down in the service elevator.

chicago sears tower skydeck

103th Floor!

I guess the service elevator wasn’t battle-ready to take on 103 floors at a time so we had to stop every 20 floors on the way down. Our timing was perfect because they shut down the entire Skydeck due to the storm! Closed for the day.

Via Twitter, I had read that all the bloggers at the Chicago Seminars were herded into a ‘safe room’ at the host hotel so I think we made out a little better than they did.

Same Day Change Ruined

As expected, the storm winds wreaked havoc at O’Hare Airport. At one point, an evacuation order was issued then cancelled, security checkpoints were closed, and there were several flight delays and cancellations.

Because of all that, my plan to Same Day Change to the Monday morning flight was shot. It was Sunday night and all the early Monday flights were zeroed out. The earliest flight I could change to was around 4:00PM Monday afternoon.

However, there was silver lining. Due to some high winds and low ceilings in the NYC area, United issued a travel waiver. That meant I could change everyone in our group (even non-elites) to the 4:00pm nonstop flight into EWR instead of the original ORD-IAD-JFK routing. That saved $75 per change! 


After a long but cheap train ride back to O’Hare, we were ready to finally go home.

Premier Access was once again a savior because regular security lines were long. The Premier Access lines were non-existent. We walked right up on the TSA agent.

I scanned my mobile boarding pass via Passbook (great app, by the way) and the machine beeped 3 times. I was excited because this meant I was cleared for TSA PreCheck! Too bad there was no PreCheck lane at this checkpoint. Come on, ORD, get with it.

We picked up some food at Tortas Frontera, a Mexican sandwich shop from Rick Bayless. If you want some good airport food at ORD Terminal B, these are some great Mexican tortas.

We crossed underground to Terminal C where our gate was and waited for boarding. I knew, by looking at the United app, that this was an internationally configured 757-200.

Too bad I didn’t have a shot in hell at a complimentary upgrade. There were about 15 people ahead of me on that list. Oh well, at least Joann and I settled in at Row 21, roomiest row on the plane!

Since this was an international plane, there was Audio/Video On Demand (AVOD) at every seat for free, unlike the domestic flights with DirectTV that you have to pay for.

Watching a classic – Stand By Me

The flight was uneventful since the weather out of Chicago was now beautiful. It was only a little rough coming into NJ since we were flying into a storm, but the pilot put us down very smoothly and just like that, we were back from our quick weekend in Chi-town.

Leaving EWR

It was our first time using long term parking P6 so we asked someone where we could catch the shuttle. FYI, it’s right across the street from the passenger pickup right outside of baggage claim. Look for the stop marked for long term parking.

We picked up the car, drove up to the exit gates, and didn’t even have to swipe a credit card thanks to E-ZPass Plus. It just went straight to our Chase Sapphire Preferred card to earn us 2 points for “travel”.

$63 to Chicago: Sights


What’s the other thing we do whenever we visit a new place? See the sights!

Chicago is a really beautiful city and I love that vantage point you can get from the Chicago River boat tours. As if the towering skyscrapers aren’t tall enough, seeing them from an even lower point of view is pretty impressive.


North Michigan Ave & Magnificent Mile

Magnificent Mile - Chicago Water Tower

Magnificent Mile – Chicago Water Tower

Wrigley Building

Wrigley Building

The Cloud Gate aka The Shiny Bean

the cloud gate chicago bean

Beautiful day at the Bean

Sears (Willis) Tower & SkyDeck

Sears (Willis) Tower

Sears (Willis) Tower… TALL


John Hancock Building – Observatory, Signature Lounge

john hancock observatory

John Hancock Observatory – Looking out at downtown Chicago from the 96th floor

Wendella Boat Tour

Sears (Willis) Tower

Sears Tower from the boat


$63 to Chicago: FOOD



We love our food whenever we visit a new destination. We managed to hit up all the places we wanted to in just over two days.

Pizzeria Due

It’s the second pizzeria opened by Ike Sewell, the founder of the famous franchise Pizzeria Uno. It’s a block north of the original Unos location and they say it’s just as good. They even share the same menu!

My first taste of Chicago deep dish in probably more than 15 years. The 4 of us shared a large Numero Uno®, since we were starving, not having eaten since early in the morning (it was now 2pm). They take your pizza order as you wait because it takes 45 minutes to make the pizza anyway.

When the pizza finally came, it was HUGE. Deep dish is serious. Layers upon layers of cheese, pepperoni, sausage, peppers, and onions smothered in a bright red tomato sauce. There’s no other way than a fork & knife for this.

Pizzeria Due uno chicago

Pizzeria Due

The Numero Uno pizzeria due

The Numero Uno

The Numero Uno pizzeria due

Serious meat & cheese layers

The Purple Pig

This is a highly rated Mediterranean tapas joint right in the heart of Downtown. Like most trendy tapas places, the place was tight and loud. The prices were actually pretty good, cheaper than any tapas place we’ve been to (Barbuto in NYC, Sra. Martinez & MGFD in Miami).

We ordered about 8 dishes between the 4 of us which was plenty as we were all still full from the pizza about 8 hours earlier. I’d say the highlights for me were the roasted bone marrow, fried brussel sprouts, pig ear & kale salad, and porchetta panini. I love tapas restaurants because you get to try so much and it’s just a more engaging eating experience with friends.

the purple pig tapas restaurant chicago

Crispy Pig Ear Salad with Kale & Egg, Burrata

the purple pig tapas restaurant chicago

Roasted Bone Marrow


We were tipped off about this Chicago institution as having good food but not specializing in anything particular. We figured it would be a good place to try both the Italian beef sandwich and a Chicago-style hot dog.

Everything was simple.. and delicious. Italian beef with spicy peppers was a perfect combo, the bread soaked with all the jus that the beef was dipped in. I had low expectations for the Chicago hot dog with all those non-meat toppings, but it all went together really well and was quite tasty. Their crinkle cut fries looked frozen but were fried perfectly. Throw some cheese sauce and chili (that tasted exactly like Fuddrucker’s) on the side and we were in heaven.

Click for the full size panorama of Portillo’s

portillos italian beef chicago hot dog

Italian Beef, Portillo’s Hot Dog, Fries, Chili and Cheese!

$63 to Chicago: CTA & Fairmont Chicago


Chicago Transit Authority

Downtown Chicago is pretty easy to get to from O’Hare Airport. Head downstairs, buy a CTA Transit Card, swipe it for $2.25, and hop on the a train on either side of the platform (headed towards Forest Park). 30-40 minutes later, you’re downtown in The Loop. As our luck would have it, the line that would take us closest to our hotel was closed for the weekend due to construction. Since it was raining, we ended up taking a short cab ride to our hotel.

Fairmont Chicago

Thanks to a late TravelZoo deal, The Fairmont Chicago had the best rate I could find for the weekend. The lobby tries to promote luxury and the room was nice, but it was nothing head and shoulders above the competition. It served just as our home base for 48 hours.

Comfortable bed, enough room to lounge around, 42″ flat screen TV with LodgeNet so you can connect to WiFi and then control your TV from your mobile device instead of a dirty remote (Android, iPhone). The best part about the hotel was definitely its location. It was a block from Wacker Drive, which runs along the Chicago River, and was basically within a mile of everything we wanted to see. Other chain hotels in the area were the Hyatt Regency, Radisson Blu, Sheraton, and InterContinental… I would just book the one with the best rate.

The only negative of our room at the Fairmont was the poorly designed bathroom. It had a walk-in shower in the corner that was undersized, along with a separate tub and separate toilet room that was small as well.