Best Travel and Hospitality Tech Companies in Chicago, United States
The 111 best Travel and Hospitality Tech companies in Chicago, United States in 2026, ranked by funding and momentum. Funding, investors, founders, valuation, tech stack and live signals. Top: The Parking Spot.
Ranked: Best Travel and Hospitality Tech companies in Chicago
| # | Company | Disclosed funding | Last round | Employees | Founded | Founder | Patents & IP focus | Recent signals |
|---|---|---|---|---|---|---|---|---|
| 1 | The Parking Spot Airport parking service provider 55Customers top 19%Funding top 32%Product top 33%Tech top 34% All 10 signals ▾Customerstop 19% Fundingtop 32% Producttop 33% Techtop 34% Innovationtop 39% Growthtop 40% Talentbottom 49% Marketbottom 48% Globalbottom 37% Fin. healthbottom 31% Customers: Play-Store rating 4.76★ across 12,681 ratings (1 apps) · Review volume +12% in 6 mo Funding: Raised $750M across 1 rounds · 1 rounds over 2 yrs (0.5/yr) rank vs industry peers · Fliar Intelligence Index 55/100 | $750M | 28 mo ago | 1,115 1,115 → 816 (-27%) | 1998 | Tony Paalz President & CEO | — | — |
| 2 | Orbitz Online travel agency | $500M | 159 mo ago | 600 | 1999 | — | 12 patents Integrated airline reservation, fare data handling, and flexible itinerary search platforms | — |
| 3 | SpotHero Provider of a platform for booking parking spots and related services | $118M | 82 mo ago | 139 139 → 298 (+114%) | 2011 | Lawrence Kiss Co-Founder | 6 patents Patents concentrated in computing, sensing & instrumentation | 2 partnerships |
| 4 | Arrive Tech-enabled platform offering parking and mobility management solutions | $65M | 91 mo ago | 1 | 2006 | Shawn Carter Co-Founder | 2 patents AI-driven natural language ambiguity resolution and privacy-preserving data processing | 1 partnership |
| 5 | Catch Online marketplace of fishing products | $56M | 61 mo ago | 80 | 2014 | Pavel Sokolovsky CEO | 6 patents Patents concentrated in chemistry & materials | — |
| 6 | Mystery Tackle Box Online e-commerce platform for fishing lures and tackle | $55M | 42 mo ago | 41 | 2012 | — | — | — |
| 7 | PriceLabs AI-powered dynamic pricing and revenue management platform for vacation rentals | $30M | 47 mo ago | 7 | 2014 | Richie Khandelwal President & Co-founder | — | 1 job opening · 1 partnership |
| 8 | Remote Year Travel subscription program while working remotely | $19M | 81 mo ago | 135 | 2015 | — | — | — |
| 9 | Telegraph Provider of cloud-based operational planning and analytics solutions for rail freight operators | $13M | 42 mo ago | 29 | 2016 | — | — | 1 partnership |
| 10 | NileGuide Local travel guides for planning trips to global destinations | $12M | 184 mo ago | 2 | 2006 | Josh Steinitz Founder & CEO | — | — |
| 11 | Rocketmiles Marketplace for hotel booking and earning reward miles | $10M | 150 mo ago | 28 | 2012 | — | — | 1 partnership |
| 12 | VacayHome Connect Provider of a distribution and marketing platform for vacation rentals | $7M | 120 mo ago | 26 26 → 25 (-4%) | 2009 | Sunil Aluvila President & CEO | — | — |
| 13 | HAAS Alert Provider of digital alerts and coordination tools for roadway safety | $5M | 29 mo ago | 41 | 2015 | Jigar Patel Co-Founder & CTO | — | 1 launch · 2 partnerships · 1 award |
| 14 | Out Of Office Online platform that provides travel recommendations from local experts | $5M | 28 mo ago | 42 | 2020 | Coabi Kastan COO + Co-Founder | — | — |
| 15 | DeepWalk LiDAR-based scanning software to automate the inspection of sidewalk systems | $2M | 37 mo ago | 8 | 2018 | Vishal Narasimhan Co-Founder | — | 1 award |
| 16 | ProvenAir Provider of AI-powered platform for aircraft records management and compliance | $2M | 23 mo ago | 13 | 2015 | James Boccarossa CEO | — | — |
| 17 | Where I've Been Interactive Travel Map | $2M | 194 mo ago | 10 | 2007 | Michael Dalesandro ex-CEO | 4 patents Travel booking and itinerary management software with graphical user interfaces | — |
| 18 | ParqEx Smart parking solutions provider unlocking value for real estate through technology | $1M | 114 mo ago | 14 | 2014 | — | — | — |
| 19 | Everpurse Wire-free charging purses blending fashion and technology for the modern woman | $1M | 145 mo ago | 4 | 2012 | — | 6 patents Wireless power transfer mats for personal electronic device charging | — |
| 20 | ApartmentJet Web-based platform for short-term rental management | $915K | 103 mo ago | 10 | 2016 | — | — | — |
| 21 | Vaystays Marketplace for luxury vacation properties rental | $750K | 145 mo ago | — | 2014 | Christopher Brusznicki Co-Founder & CEO | — | — |
| 22 | Twisted road Online P2P motorbike rental paltform | $615K | 82 mo ago | 3 | 2017 | — | — | 1 partnership |
| 23 | OpenAirplane Operator of a network that facilitated airplane rentals for qualified pilots | $500K | 124 mo ago | 3 | 2012 | Rod Rakic Co-Founder | — | — |
| 24 | ThruGreen Provider of traffic-signal control and management solutions | $345K | 53 mo ago | 7 | 2016 | David Nguyen Founder | 31 patents Adaptive traffic signal control and connected vehicle infrastructure for dynamic traffic management | — |
| 25 | Tripnary App-based travel planning platform | $200K | 142 mo ago | 3 | 2013 | Abhishek Ghuwalewala Founder & CEO | — | — |
| 26 | Foresyte App-based community platform for travelers | $200K | 49 mo ago | 6 | 2022 | Dani Hristeva Co-Founder | — | — |
| 27 | Fueloyal Technology IoT & connected vehicle platform provider enabling data monetization and vehicle connectivity | $124K | 99 mo ago | 11 | 2015 | — | — | — |
| 28 | Airfordable Fly now, pay later: Flexible flight installment plans | $120K | 120 mo ago | 7 | 2016 | — | — | — |
| 29 | PiggyBack Online platform offering ride-pooling services | $100K | 52 mo ago | 6 | 2020 | Donald Scott Co-Founder | — | — |
Top 12 Travel and Hospitality Tech companies in Chicago
#1
Acquired · Chicago, Illinois · founded 1998 · 1115 employees$750Mraised▾
The Parking Spot provides parking services at airports. Users can book parking spots available at airports via the online platform. Users can use their membership cards to open the parking barriers at the entry & exit of the parking slot. Also provides airport shuttle & valet parking services. Offers corporate airport parking services.
- Feb 2024Conventional Debt$750M
#2
Series A · Chicago, Illinois · founded 2015 · 13 employees$1.8Mraised▾
Provider of AI-powered platform for aircraft records management and compliance. The platform digitizes and analyzes aircraft documentation to ensure accuracy and traceability of life-limited parts. It offers features such as document processing, digital trace insights, and automated verification. The platform generates audit-ready reports and facilitates online collaboration for analysts. It helps lessors, airlines, MROs, and suppliers with trace analysis.
- Jul 2024Series A$3M
#3
Series B · Chicago, Illinois · founded 2012 · 41 employees$55Mraised▾
Online e-commerce platform for fishing lures and tackle. The platform provides users with fishing products. Users can choose the plan from the platform and receive it on a subscription basis. It offers a mixture of full retail package hard baits and sample packages of terminal tackle and soft plastics.
- Dec 2022Series B$9.3M
- Aug 2022Series B$2.7M
- Apr 2021Series B$38M
- Dec 2020Series A$4.9M
#4
Seed · Chicago, Illinois · founded 2015 · 41 employees$5.1Mraised▾
Provider of digital alerts and coordination tools for roadway safety. The company delivers real-time digital alerts to protect responders, workers, and drivers. It offers tools for emergency vehicle alerting, responder-to-responder coordination, and emergency vehicle preemption. The company provides solutions for automotive, DOTs, fire and EMS, government, law enforcement, towing, utility, and work zones. It allows users to manage fleets in real time.
- Jan 2024Seed—
- Aug 2021Seed$5M
- Oct 2018Grant (prize money)$1.1M
- 2018Grant (prize money)—
#5
Series A · Chicago, Illinois · founded 2020 · 42 employees$5Mraised▾
Online platform that provides travel recommendations from local experts. Travelers can build a wishlist of places they want to go, create trips, add places to them, collaborate with friends, make bookings & more.
- Jan 2024Series A$1.3M
- Apr 2022Series A$3.5M
#6
Series A · Chicago, Illinois · founded 2016 · 29 employees$13.3Mraised▾
Provider of cloud-enabled operational planning and analytics solutions for rail freight operators. The solution helps in managing rail freight workflow operations. It also helps in managing supply chain freight visibility, asset management, collaborations, optimized pricing, and more.
- Dec 2022Series A$10.1M
- Seed$3.2M
#7
Series A · Chicago, Illinois · founded 2014 · 7 employees$30Mraised▾
AI-powered dynamic pricing and revenue management platform for vacation rentals. It offers data-driven pricing automation, portfolio analytics, and actionable market insights. The platform provides solutions for Airbnb hosts, Vrbo hosts, property managers, hotels, aparthotels, mid-term rentals, campgrounds, villas, and chalets. It connects with numerous PMS and channel managers, offering features for property managers and hosts. The platform utilizes a hyper-local pulse algorithm for intelligent price recommendations, considering market trends, supply, demand, seasons, events, and holidays. It offers customizable data-driven smart pricing, advanced minimum stay intelligence, and time-saving workflows. It provides tools like market dashboards, revenue estimator, booking analyzer, and Airbnb description generator. It is a SaaS platform that helps users to increase revenue and occupancy. It offers subscription based pricing. It is a cloud based software.
- Jun 2022Series A$30M
#8
Acquired · Chicago, Illinois · founded 2011 · 139 employees$118.3Mraised▾
Provider of a platform for booking parking spots and related services. The platform allows users to search and reserve parking spaces. It offers options for hourly, daily, and monthly parking. The platform also provides booking capabilities through mobile applications and integration with vehicle dashboards.
- Aug 2019Series D$50M
- Nov 2018Series C$124.2K
- Sep 2018Series C$10M
- Jul 2017Series C$31.2M
#9
Acquired · Chicago, Illinois · founded 2014 · 80 employees$56Mraised▾
Online marketplace of fishing products. Travelers can discover & buy products via the platform & can make an online payment.
- Apr 2021Series B$38M
- Dec 2020Series B$6M
- Oct 2017Series A$3.5M
#10
Acquired · Chicago, Illinois · founded 1999 · 600 employees$500Mraised▾
Orbitz.com is a part of Orbitz Worldwide which operates other online travel sites: ebookers, CheapTickets and HotelClub. Orbitz lets users book online flight tickets, hotels, cars, activities, and cruises. It also offers Orbitz credits points which can be redeemed by frequent flyers. In Dec. 2003 the company went pubic and in Sept. 2004, it was acquired by Cendant Corporation for $1.25 billion, which rolled Oribitz into its online travel segment, named Travelport. Cedant then sold Travelport to private equity firm Blackstone Group in June 2006. Blackstone and Travelport spun off Orbitz to the public market in July 2007. In February 2015, Expedia announced that it would acquire Orbitz for $1.2 billion in cash.
- Mar 2013Conventional Debt$500M
#11
Series D · Chicago, Illinois · founded 2006 · 1 employees$65.3Mraised▾
Arrive offers a tech-enabled platform offering parking and mobility management solutions. The platform offers integrated solutions for parking management, transit solutions, and more. It connects consumers and operators/owners over a single platform. Users can do on-off street parking, event parking management, white-lable parking solutions for apartments and closed community, etc.
- Nov 2018Series D$5M
- Sep 2018Series D$21.8M
- Mar 2018Conventional Debt—
- Mar 2018Series C—
#12
Seed · Chicago, Illinois · founded 2018 · 8 employees$1.8Mraised▾
LiDAR-based scanning software to automate the inspection of sidewalk systems. The platform offers software that uses LiDAR systems to automatically scan and identify non-compliant areas.
- May 2023Seed$1.4M
- Apr 2019Grant (prize money)$75K
Funding & investor landscape
Notable founders
Market landscape — 10 sub-themes by coverage
Share of Travel and Hospitality Tech coverage by sub-theme.
Regulatory-risk over time rising
Funding & growth over time
funding rising · growth rising
Common questions
Sweetie watches where the money and the users are piling in. She covers sector wealth and momentum — the install curves and revenue pools that show which corners of the market are quietly on fire.