$45 Cheap flight deals from Chicago (CHI) to Cypress (HOU)

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This Weekend's Flight Deals from Chicago to Cypress

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Oct 11 - Sat, Oct 18
MDW
Midway Intl.
IAH
George Bush Intercontinental
$124 Roundtrip, found 5 days ago
$124
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Oct 11 from Midway Intl. to George Bush Intercontinental, returning Sat, Oct 18, priced at $124 found 5 days ago
Sat, Oct 11 - Sat, Oct 18
MDW
Midway Intl.
IAH
George Bush Intercontinental
$124 Roundtrip, found 5 days ago
$124
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Oct 11 from Midway Intl. to George Bush Intercontinental, returning Sat, Oct 18, priced at $124 found 5 days ago
Sun, Oct 12 - Sat, Nov 1
ORD
O'Hare Intl.
IAH
George Bush Intercontinental
$177 Roundtrip, just found
$177
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Oct 12 from O'Hare Intl. to George Bush Intercontinental, returning Sat, Nov 1, priced at $177 just found
Sun, Oct 12 - Sat, Nov 1
ORD
O'Hare Intl.
IAH
George Bush Intercontinental
$177 Roundtrip, just found
$177
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Oct 12 from O'Hare Intl. to George Bush Intercontinental, returning Sat, Nov 1, priced at $177 just found

Airfares from $45 One Way, $88 Round Trip from Chicago to Cypress

Prices starting at $88 for return flights and $45 for one-way flights to Cypress were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Oct 25 - Sat, Nov 1
MDW
Chicago
IAH
Houston
$88 Roundtrip, found 1 day ago
$88
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Oct 25 from Chicago to Houston, returning Sat, Nov 1, priced at $88 found 1 day ago
Wed, Dec 3 - Sat, Dec 6
ORD
Chicago
IAH
Houston
$90 Roundtrip, found 2 hours ago
$90
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Wed, Dec 3 from Chicago to Houston, returning Sat, Dec 6, priced at $90 found 2 hours ago
Thu, Jan 1 - Sat, Jan 10
MDW
Chicago
HOU
Houston
$168 Roundtrip, found 8 hours ago
$168
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Thu, Jan 1 from Chicago to Houston, returning Sat, Jan 10, priced at $168 found 8 hours ago
Sat, Dec 6 - Mon, Dec 8
RFD
Rockford
IAH
Houston
$177 Roundtrip, found 4 hours ago
$177
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, Dec 6 from Rockford to Houston, returning Mon, Dec 8, priced at $177 found 4 hours ago
Sat, Dec 6 - Mon, Dec 8
ORD
Chicago
IAH
Houston
$177 Roundtrip, found 11 hours ago
$177
Roundtrip
found 11 hours ago
Select United flight, departing Sat, Dec 6 from Chicago to Houston, returning Mon, Dec 8, priced at $177 found 11 hours ago

Cypress economy flight packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel & Suites Houston by the Galleria
4.0-star property

DoubleTree by Hilton Hotel & Suites Houston by the Galleria

8.2/10 Very Good! (2,530 reviews)

Nov 13 - Nov 16

3 night stay

Chicago (CHI) to Houston (IAH)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $424, price is now $282 per person
$282
per person
found 1 day ago
The location was amazing. The facility was clean. The wait staff was great. However, front desk was drastically understaffed with line out the door on several occasions. The check in process can be smoother as the valet said you had to pay inside; you go inside and wait in the line for 30 mins and front desk says you are to pay valet outside.

Reviewed on Sep 30, 2025

Hotel Granduca Houston
4.0-star property

Hotel Granduca Houston

9.2/10 Wonderful! (1,007 reviews)

Nov 13 - Nov 16

3 night stay

Chicago (CHI) to Houston (IAH)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $918, price is now $603 per person
$603
per person
found 1 day ago
The management and employees are very professional and friendly. I continue to stay there as it's an excellent location as well

Reviewed on May 20, 2025

Holiday Inn Houston Downtown by IHG
3.0-star property

Holiday Inn Houston Downtown by IHG

8.8/10 Excellent! (1,464 reviews)

Nov 13 - Nov 17

4 night stay

Chicago (CHI) to Houston (IAH)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $827, price is now $544 per person
$544
per person
found 1 day ago
Great facilities and services. But not many walking distance restaurants nearby to choose from.

Reviewed on Jun 17, 2025

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More About Flying To Cypress from Chicago

Route Information for Flights from Chicago to Cypress

Origin Airport IATA Code
CHI
Destination Airport IATA Code
HOU
Distance
925 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Austrian, Aer Lingus, Emirates, Air New Zealand, United Airlines, Alaska Airlines, Frontier Airlines, Avianca, Royal Jordanian, Iberia, ANA, Brussels Airlines, Lufthansa, Spirit Airlines, British Airways, Gulf Air
Earliest Flight Arrival
1:51PM UTC
Latest Flight Arrival
4:56AM UTC

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.