Best Online Travel Companies in Chicago, United States
The 46 best Online Travel companies in Chicago, United States in 2026, ranked by funding and momentum. Funding, investors, founders, valuation, tech stack and live signals. Top: Orbitz.
Ranked: Best Online Travel companies in Chicago
| # | Company | Disclosed funding | Last round | Stage | Founder | Founded | Tech stack | Patents & IP focus | Recent signals |
|---|---|---|---|---|---|---|---|---|---|
| 1 | Orbitz Online travel agency | $500M | 161 mo ago | Acquired | — | 1999 | Apple iCloud MailTypeScriptGraphQL+24 | 12 patents Travel reservation and itinerary management software integrating fare data and flexible search | — |
| 2 | Catch Online marketplace of fishing products | $56M | 63 mo ago | Acquired | Pavel Sokolovsky CEO | 2014 | Builder.ioAmazon Web ServicesSendgrid+7 | 6 patents Enzymatic assay kits for quantifying homocysteine/cystathionine in clinical samples | — |
| 3 | Mystery Tackle Box Online e-commerce platform for fishing lures and tackle | $55M | 44 mo ago | Series B | — | 2012 | Cart FunctionalityShopifyBuilder.io+38 | — | — |
| 4 | Remote Year Travel subscription program while working remotely | $19M | 83 mo ago | Acquired | — | 2015 | BootstrapAmazon ALBAmazon Web Services+4 | — | — |
| 5 | NileGuide Local travel guides for planning trips to global destinations | $12M | 186 mo ago | Acquired | Josh Steinitz Founder & CEO | 2006 | NginxjQuery UIjQuery+5 | — | — |
| 6 | Rocketmiles Marketplace for hotel booking and earning reward miles | $10M | 152 mo ago | Acquired | — | 2012 | Builder.ioJavaChakra UI+20 | — | 1 partnership |
| 7 | VacayHome Connect Provider of a distribution and marketing platform for vacation rentals | $7M | 122 mo ago | Series A | Sunil Aluvila President & CEO | 2009 | WordPressMySQLPHP+20 | — | — |
| 8 | Out Of Office Online platform that provides travel recommendations from local experts | $5M | 30 mo ago | Series A | Coabi Kastan COO + Co-Founder | 2020 | — | — | — |
| 9 | Where I've Been Interactive Travel Map | $2M | 196 mo ago | Acqui-Hired | Michael Dalesandro ex-CEO | 2007 | — | 4 patents Travel e‑commerce platforms with graphical user interfaces for booking and itinerary management | — |
| 10 | Everpurse Wire-free charging purses blending fashion and technology for the modern woman | $1M | 147 mo ago | Seed | — | 2012 | — | 6 patents Inductive wireless charging mats for personal electronic devices | — |
| 11 | ApartmentJet Web-based platform for short-term rental management | $915K | 105 mo ago | Acquired | — | 2016 | — | — | — |
| 12 | Vaystays Marketplace for luxury vacation properties rental | $750K | 147 mo ago | Seed | Christopher Brusznicki Co-Founder & CEO | 2014 | — | — | — |
| 13 | OpenAirplane Operator of a network that facilitated airplane rentals for qualified pilots | $500K | 126 mo ago | Seed | Rod Rakic Co-Founder | 2012 | — | — | — |
| 14 | Tripnary App-based travel planning platform | $200K | 144 mo ago | Deadpooled | Abhishek Ghuwalewala Founder & CEO | 2013 | — | — | — |
| 15 | Foresyte App-based community platform for travelers | $200K | 51 mo ago | Seed | Dani Hristeva Co-Founder | 2022 | WordPress Block EditorWordPressMySQL+14 | — | — |
| 16 | Airfordable Fly now, pay later: Flexible flight installment plans | $120K | 122 mo ago | Seed | — | 2016 | SentryTypeScriptGraphQL+22 | — | — |
Top 12 Online Travel companies in Chicago
#1
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
#2
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
#3
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
#4
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
#5
Acquired · Chicago, Illinois · founded 2015 · 135 employees$19.2Mraised▾
Remote year is a one year subscription program where there will be a $2,000 fee on the 1st of every month of Remote Year in addition to a $3,000 down payment to reserve a spot, this includes all commute and accommodation costs for a period of 1 year. The participants can work remotely if they get a job on their own.
- Sep 2019Series A$7M
- Oct 2016Series A$12M
- May 2015Seed$175K
#6
Series A · Chicago, Illinois · founded 2009 · 26 employees$7.1Mraised▾
VacayHome Connect is the provider of a distribution and marketing platform for vacation rentals. Its features include channel management, digital marketing, content management and optimization, membership, and loyalty distribution, and more. It can also be integrated with existing CMS and PMS. Its clients include Canyon Services, Vacation Rental Pros, HomeAway, and others.
- Jun 2016Series A$685K
- Aug 2015Series A$4.1M
- Nov 2014Series A$2.3M
- Oct 2014Series A$4.1M
#7
Acquired · Chicago, Illinois · founded 2006 · 2 employees$11.7Mraised▾
Local travel guides for planning trips to global destinations. This platform provides recommendations for exploring popular travel destinations worldwide. It offers local insights on the best things to do, hotels, restaurants, and attractions. Users can plan trips to various locations across North America, Europe, South America, the Caribbean, Oceania, Central America, Asia, and Africa. The service aims to provide a local perspective for travelers seeking authentic experiences. It is a resource for individuals looking to explore and discover new places with insider knowledge. The platform supports travel planning by offering curated information and recommendations.
- Feb 2011Venture Debt—
- Dec 2010Series C$3.5M
- Aug 2010Series B$200K
- Jun 2008Series B$8M
#8
Seed · Chicago, Illinois · founded 2022 · 6 employees$199.9Kraised▾
App-based community platform for travelers. Users can create itineraries through the platform by communicating with other users. App is available for both Android and iOS devices.
- May 2022Seed$199.9K
#9
Acquired · Chicago, Illinois · founded 2012 · 28 employees$10.3Mraised▾
Rocketmiles buys miles from airlines which it then links to stays with its partner hotels. Customers earn an average of 7,000 miles per booking. It basically focuses on delivering hand picked hotels at the same price as other aggregators. The company buys its hotel rooms at a lower rate and resells them at a higher price, earning revenue to purchase miles for its customers.
- Dec 2013Series A$8.3M
- Apr 2013Seed$2M
#10
Acqui-Hired · Chicago, Illinois · founded 2007 · 10 employees$1.8Mraised▾
Where I've Been is a social networking application that marked its users' travel history on a color-coded map. The site collected user-generated content such as photos, videos and reviews. It is a personalized and interactive world map that lets users share their travels.
- Apr 2010Seed$750K
- Angel$1M
#11
Acquired · Chicago, Illinois · founded 2016 · 10 employees$915Kraised▾
ApartmentJet provides an online platform for property management of short-term rentals. Customers can list apartments, manage content, communicate with guests and monitor performance of units. The platform is integrated with a screening solution which performs a background check and automatically responds to a booking request. It also provides an insurance cover through a partner for damage and liability. As of Oct 2017, it charges 10% of fee per stay.
- Nov 2017Seed$915K
#12
Seed · Chicago, Illinois · founded 2012 · 4 employees$1Mraised▾
Wire-free charging purses blending fashion and technology for the modern woman. This company builds a tech platform for handbags, seamlessly integrating technology to enhance the user experience without compromising design. They offer wire-free mobile charging, handbag tracking, and item authentication. Their guiding principle is to enhance the experience without changing the design. They eliminate wires, buttons, and techy elements, focusing on fashion and function. The company empowers brands to create deeper relationships with customers through innovative technology. They offer a tech platform for handbags, mobile charging, tracking, and authentication. They are focused on fashion, technology, wire-free, mobile charging, handbag, tracking, authentication, B2C, e-commerce, cart, login, shop now.
- May 2014Seed$1M
Funding & investor landscape
Notable founders
Market landscape — 10 sub-themes by coverage
Share of Online Travel coverage by sub-theme.
Regulatory-risk over time rising
Funding & growth over time
funding rising · growth rising
Common questions
Riya reads income statements for fun. She covers the real money in a sector — revenue, growth, who actually earns — and never met a vague claim she didn't want a number for.