Ever need to just get away for a weekend? Looking for an adventure?
You can get great last minute deals on trips to Chicago for less than the cost of a regular flight!
By using Google Fights, I looked around and found round-trip plane tickets from Phoenix (where I live) to Chicago for about $100! For reference, that's about a quarter of the usual cost.
Our flight was on Frontier Airlines, which, to be fair, is not the most glamorous airline. We only brought one backpack each, avoiding the additional $30 (each way) fee to put a bag in the overhead carrier, and even more by not checking a bag. The flight was on time, and we even arrived at our destination early!
Through the Frontier site, because we booked a flight, we got special deals on participating hotels. We ended up getting a top floor, king-size bedroom in Downtown Chicago, right on the river, about 2 blocks from Millenium Park, 3 blocks from Navy Pier, and a short distance to lots of food and shopping. All this cost us less than $100/night to stay at the Hyatt Regency Chicago.
I ended up getting about half off of admission to the observation deck in John Hancock Tower from Groupon here. This cost me about $20 for 2 tickets.
Here was our basic itinerary for the weekend:
Wednesday-
Booked flight, travel insurance, groupon deals & hotel
Friday-
10 AM - 3 PM: Flight from PHX to ORD
3 PM: Blue line "L" to Downtown Chicago
4 PM: Check into hotel
6 PM: Shopping
7 PM: Dinner at Lou Malnati's
9 PM: Enjoy coffee, Netflix, and good company while looking at the beautiful skyline
Saturday-
11 AM: Brunch at Toni's Patisserie and Cafe
12:30 PM: Looking and exploring "The Bean" and surrounding attractions
2 PM: Ice Skating at Millenium Park
3:30 PM: Protein Smoothies
5 PM: 360 Observation Deck (Gelato inside)
8 PM: Dinner at M Burger
9 PM: Window Shopping in Water Tower Place
10:30 PM: Coffee and snacks at Argo Tea
11:30 PM: Workout in the Hyatt's Fitness Center
1 AM: Late-night Pizza delivered by Uber Eats
Sunday-
11 PM: Brunch at Le Pain Quotidien
1 PM: Blue line "L" to Downtown Chicago
4 PM - 7 PM: Flight from ORD to PHX
Overall, the trip cost each of us less than $325.
The reason we were able to get such a good deal on this trip was because we went in the off-season. Chicago in January is COLD. However, with a thick sweater, a good blanket scarf, and a faux-leather jacket, I was able to stay nice and cozy.
COST (Individual):
$129.35 - Round-trip Plane Ticket and Travel insurance
$102.08 - Hotel for 2 nights
$10 - Blue Line tickets
$5.50 - Dinner at Lou Malnati's (We ended up getting a free pizza)
$10.54 - Toni's Patisserie and Cafe
$12 - Ice skating
$3.34 - Smoothie
$11.00 - 360 Observation Deck (after coupon and Groupon $10 off)
$9.28 - Dinner at M Burger
$6.70 - Argo Tea
$10.67 - Uber Eats delivered Pizza (approx. $5 fee for delivery)
$13.66 - Le Pain Quotidien
Total: $324.12
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